3-heteroaryl substituted 5-methyloxymethyl isoxazolines used as herbicides

ABSTRACT

3-Heteroaryl-substituted isoxazolines of the formula I 
                         
where:
     X is substituted 5-membered heteroaryl having one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or sulfur atom or one oxygen or sulfur atom; or
       substituted 6-membered heteroaryl having one to four nitrogen atoms;   where the abovementioned 5-membered heteroaryl is not pyrazolyl or thienyl;   
       R 1 -R 7  are hydrogen, alkyl or haloalkyl;   Y is unsubstituted or substituted aryl, or benzo[1,4]dioxonyl, benzo[1,3]dioxolanyl, 2,3-dihydrobenzofuranyl or benzimidazole; or
       unsubstituted or substituted 5- to 6-membered heteroaryl;   and their agriculturally useful salts,
 
processes and intermediates for their preparation, and the use of these compounds or of the compositions comprising these compounds for controlling unwanted plants are described.

The present invention relates to 3-heteroaryl-substituted isoxazolines of the formula I

where:

-   -   X is 5-membered heteroaryl having one to four nitrogen atoms or         one to three nitrogen atoms and one oxygen or sulfur atom or one         oxygen or sulfur atom; or         -   is 6-membered heteroaryl having one to four nitrogen atoms,         -   where the heterocycles are partially or fully halogenated             and/or carry one to three substituents selected from the             following group:         -   cyano, nitro, hydroxyl, C₁-C₈-alkyl, C₃-C₆-cycloalkyl,             C₃-C₆-halocycloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl,             C₁-C₈-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,             C₁-C₈-cyanoalkyl, C₂-C₈-cyanoalkenyl, C₁-C₈-alkoxy,             C₁-C₈-haloalkoxy, C₁-C₈-alkoxy-C₁-C₈-alkyl,             C₁-C₈-alkoxy-C₁-C₈-alkoxy, amino, C₁-C₈-alkylamino,             di(C₁-C₈-alkyl)amino, C₁-C₈-alkylcarbonylamino,             N—C₁-C₈-alkylcarbonyl-N—C₁-C₈-alkylamino,             C₁-C₈-alkoxycarbonylamino,             N—C₁-C₈-alkoxycarbonyl-N—C₁-C₈-alkylamino,             amino-C₁-C₈-alkyl, C₁-C₈-alkylamino-C₁-C₈-alkyl,             di(C₁-C₈-alkyl)amino-C₁-C₈-alkyl, C₁-C₈-alkylthio,             C₁-C₈-haloalkylthio, C₁-C₈-alkylthio-C₁-C₈-alkyl,             C₁-C₈-alkylsulfinyl, C₁-C₈-haloalkylsulfinyl,             C₁-C₈-alkylsulfonyl, C₁-C₈-haloalkylsulfonyl,             C₁-C₈-alkylsulfonyl-C₁-C₈-alkyl, C₁-C₈-alkylcarbonyl,             C₁-C₈-alkoxycarbonyl, C₁-C₈-alkoxycarbonyl-C₁-C₈-alkyl,             aminocarbonyl, C₁-C₈-alkylaminocarbonyl,             di(C₁-C₈-alkyl)aminocarbonyl, aminocarbonyl-C₁-C₈-alkyl,             C₁-C₈-alkylaminocarbonyl-C₁-C₈-alkyl,             di(C₁-C₈-alkyl)aminocarbonyl-C₁-C₈-alkyl, carboxyl,             carboxy-C₁-C₈-alkyl, phenyl, phenoxy, phenylthio,             phenylamino, phenyl-C₁-C₈-alkyl, phenyl-C₁-C₈-alkoxy, 3- to             6-membered heterocyclyl and 5- to 6-membered heteroaryl,             where the eight last-mentioned radicals for their part may             be partially or fully halogenated and/or may carry one to             three substituents selected from the group consisting of             nitro, cyano, C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-haloalkyl,             C₁-C₈-haloalkoxy, C₁-C₈-alkylthio, C₁-C₈-haloalkylthio,             C₁-C₈-alkylsulfinyl, C₁-C₈-haloalkylsulfinyl,             C₁-C₈-alkylsulfonyl and C₁-C₈-haloalkylsulfonyl;         -   where the abovementioned 5-membered heteroaryl is not             pyrazolyl or thienyl;     -   R¹-R⁷ are hydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl;     -   Y is aryl which may be partially or fully halogenated and/or may         carry one to three substituents selected from the group         consisting of cyano, nitro, C₁-C₆-alkyl, C₂-C₆-alkenyl,         C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,         C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkoxycarbonyl,         C₁-C₆-alkoxycarbonyl-C₁-C₄-alkoxy, C₁-C₆-alkylsulfonyl, phenyl,         phenoxy and phenylcarbonyl, benzo[1,4]dioxonyl,         benzo[1,3]dioxolanyl, 2,3-dihydrobenzofuranyl or benzimidazole;         or         -   5-membered heteroaryl having one to four nitrogen atoms or             having one to three nitrogen atoms and one oxygen or sulfur             atom or having one oxygen or sulfur atom; or         -   6-membered heteroaryl having one to four nitrogen atoms;             where the heterocycles may be partially or fully halogenated             and/or may carry one to three substituents from the group             consisting of cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,             C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxycarbonyl and             C₁-C₆-alkylsulfonyl;             and their agriculturally useful salts.

Moreover, the invention relates to processes and intermediates for preparing compounds of the formula I, to compositions comprising them and to the use of these derivatives or of the compositions comprising them for controlling harmful plants.

3-phenyl-substituted isoxazolines are known from the literature, for example from EP 514 987. EP 334 120 discloses isoxazolines which are substituted in the 3-position by an unsubstituted heterocycle. Furthermore, JP 2001/158787 describes 3-pyrazolyl-substituted isoxazolines. WO 02/19825 and KR 2002/19751 disclose thienyl-substituted isoxazolines. JP 09/143,171 mentions isoxazolines which are substituted in the 3-position by a carbonyl or oxime group.

However, the herbicidal properties of the prior-art compounds and their compatibility with crop plants are not entirely satisfactory.

It is an object of the present invention to provide novel, in particular herbicidally active, compounds having improved properties.

We have found that this object is achieved by the 3-heteroaryl-substituted isoxazolines of the formula I and their herbicidal action.

Furthermore, we have found herbicidal compositions which comprise compounds I and have very good herbicidal action. Moreover, we have found processes for preparing these compositions and methods for controlling unwanted vegetation using the compounds I.

Depending on the substitution pattern, the compounds of the formula I may contain one or more centers of chirality, in which case they are present as enantiomers or mixtures of diastereomers. The invention provides both the pure enantiomers or diastereomers and their mixtures.

The compounds of the formula I may also be present in the form of their agriculturally useful salts, the type of salt generally being immaterial. In general, suitable salts are the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the herbicidal action of the compounds I.

Suitable cations are in particular ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium, where, if desired, one to four hydrogen atoms may be replaced by C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, hydrogencarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C₁-C₄-alkanoic acids, preferably formate, acetate, propionate and butyrate.

The organic moieties mentioned for the substituents R¹-R⁷ or as radicals on aryl or heteroaryl rings are collective terms for individual enumerations of the individual group members. All hydrocarbon chains, i.e. all alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkylcarbonyloxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylamino, dialkylamino, alkylcarbonylamino, N-alkylcarbonyl-N-alkylamino; alkoxyalkyl, alkoxyalkoxy, alkylthioalkyl, dialkylaminoalkyl and alkoxycarbonylalkyl moieties, may be straight-chain or branched. Unless indicated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms. In each case, the term “halogen” denotes fluorine, chlorine, bromine or iodine.

Examples of other meanings are:

-   -   C₁-C₄-alkyl and the alkyl moieties of C₁-C₄-alkoxy-C₁-C₄-alkyl,         C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl,         C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonylamino,         N—C₁-C₄-alkylcarbonyl-N—C₁-C₄-alkylamino,         N—C₁-C₄-alkoxycarbonyl-N—C₁-C₄-alkylamino, amino-C₁-C₄-alkyl,         C₁-C₄-alkylamino-C₁-C₄-alkyl, di(C₁-C₄-alkyl)amino-C₁-C₄-alkyl,         carboxy-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,         aminocarbonyl-C₁-C₄-alkyl, C₁-C₄-alkylaminocarbonyl-C₁-C₄-alkyl,         di(C₁-C₄-alkyl)aminocarbonyl-C₁-C₄-alkyl and phenyl-C₁-C₄-alkyl:         for example methyl, ethyl, propyl, 1-methylethyl, butyl,         1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;     -   C₁-C₆-alkyl: C₁-C₄-alkyl as mentioned above, and the alkyl         moieties of C₁-C₆-alkoxy-C₁-C₆-alkyl,         C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl,         C₁-C₆-alkylcarbonyl, C₁-C₆-alkylcarbonylamino,         N—C₁-C₆-alkylcarbonyl-N—C₁-C₆-alkylamino,         N—C₁-C₆-alkoxycarbonyl-N—C₁-C₆-alkylamino, amino-C₁-C₆-alkyl,         C₁-C₆-alkylamino-C₁-C₆-alkyl, di(C₁-C₆-alkyl)amino-C₁-C₆-alkyl,         carboxy-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl,         aminocarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylaminocarbonyl-C₁-C₆-alkyl,         di(C₁-C₆-alkyl)aminocarbonyl-C₁-C₆-alkyl and phenyl-C₁-C₆-alkyl;         and also, for example, pentyl, 1-methylbutyl, 2-methylbutyl,         3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl,         1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl,         2-methylpentyl, 3-methylpentyl, 4-methylpentyl,         1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,         2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,         1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,         1-ethyl-1-methylpropyl and 1-ethyl-3-methylpropyl;     -   C₁-C₈-alkyl: C₁-C₆-alkyl as mentioned above, and the alkyl         moieties of C₁-C₈-alkoxy-C₁-C₈-alkyl,         C₁-C₈-alkylthio-C₁-C₈-alkyl, C₁-C₈-alkylsulfonyl-C₁-C₈-alkyl,         C₁-C₈-alkylcarbonyl, C₁-C₈-alkylcarbonylamino,         N—C₁-C₈-alkylcarbonyl-N—C₁-C₈-alkylamino,         N—C₁-C₈-alkoxycarbonyl-N—C₁-C₈-alkylamino, amino-C₁-C₈-alkyl,         C₁-C₈-alkylamino-C₁-C₈-alkyl, di(C₁-C₈-alkyl)amino-C₁-C₈-alkyl,         carboxy-C₁-C₈-alkyl, C₁-C₈-alkoxycarbonyl-C₁-C₈-alkyl,         aminocarbonyl-C₁-C₈-alkyl, C₁-C₈-alkylaminocarbonyl-C₁-C₈-alkyl,         di(C₁-C₈-alkyl)aminocarbonyl-C₁-C₈-alkyl and phenyl-C₁-C₈-alkyl,         and also, for example, heptyl, 2-methylhexyl, 3-methylhexyl,         2,2-dimethylpentyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl,         3,3-dimethylpentyl, 2,2,3-trimethylbutyl, octyl, 2-methylheptyl,         3-methylheptyl, 4-methylheptyl, 2,2-dimethylhexyl,         2,3-dimethylhexyl, 2,4-dimethylhexyl, 3,3-dimethylhexyl,         2,2,3-trimethylpentyl, 2,3,3-trimethylpentyl,         2,3,4-trimethylpentyl and 2,2,3,3-tetramethylbutyl;     -   C₃-C₆-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl and         cyclohexyl;     -   C₃-C₆-halocycloalkyl: C₃-C₆-cycloalkyl, as mentioned above which         is partially or fully substituted by fluorine, chlorine, bromine         and/or iodine, i.e., for example, 2,2-difluorocyclopropyl,         2,2-dichlorocyclopropyl, 3-fluorocyclopentyl,         3-chlorocyclopentyl, 3,3-difluorocyclopentyl,         3,3-dichlorocyclopentyl, 4-fluorocyclohexyl, 4-chlorocyclohexyl,         4,4-difluorocyclohexyl and 4,4-dichlorocyclohexyl;     -   three- to six-membered heterocyclyl: a monocyclic saturated or         partially unsaturated hydrocarbon having three to six ring         members as mentioned above which may, in addition to carbon         atoms, comprise one to four nitrogen atoms or one to three         nitrogen atoms and one oxygen or sulfur atom or one oxygen         and/or one sulfur atom or 2 oxygen or 2 sulfur atoms and which         may be attached via a carbon atom or a nitrogen atom, for         example         -   3- to 4-membered heterocyclyl:         -   2-oxiranyl, 2-oxetanyl, 3-oxetanyl, 2-aziridinyl,             3-thiethanyl, 1-azetinyl, 2-azetinyl;         -   5-membered saturated heterocyclyl attached via a carbon             atom:         -   2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 1,3-dioxolan-2-yl,             1,3-dioxolan-5-yl, 2-tetrahydrothienyl, 3-tetrahydrothienyl,             1,3-dithiolan-2-yl, 1,3-dithiolan-5-yl, 1,2-dithiolan-3-yl,             1,2-dithiolan-4-yl, 2-pyrrolidinyl, 3-pyrrolidinyl,             3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl,             3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl,             3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl,             2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl,             2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl,             2-imidazolidinyl, 4-imidazolidinyl,             1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,             1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,             1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl,             1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl;         -   5-membered saturated heterocyclyl attached via a nitrogen             atom:         -   1-pyrrolidinyl, 2-isothiazolidinyl, 2-isothiazolidinyl,             1-pyrazolidinyl, 3-oxazolidinyl, 3-thiazolidinyl,             1-imidazolidinyl, 1,2,4-triazolidin-1-yl,             1,2,4-oxadiazolidin-2-yl, 1,2,4-oxadiazolidin-4-yl,             1,2,4-thiadiazolidin-2-yl, 1,2,4-thiadiazolidin-4-yl;         -   5-membered partially unsaturated heterocyclyl attached via a             carbon atom:         -   2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl,             2,3-dihydrofur-4-yl, 2,4-dihydrofur-2-yl,             2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl,             2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl,             2,4-dihydrothien-3-yl, 4,5-dihydropyrrol-2-yl,             4,5-dihydropyrrol-3-yl, 2,5-dihydropyrrol-2-yl,             2,5-dihydropyrrol-3-yl, 4,5-dihydroisoxazol-3-yl,             2,5-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-3-yl,             4,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-4-yl,             2,3-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl,             2,5-dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-5-yl,             4,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-3-yl,             2,3-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl,             2,5-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-4-yl,             4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-5-yl,             2,3-dihydroisothiazol-5-yl, 2,3-dihydropyrazol-3-yl,             2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl,             3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl,             3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-3-yl,             4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl,             2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-4-yl,             2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl,             4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl,             2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl,             2,5-dihydroimidazol-5-yl, 2,3-dihydrooxozol-2-yl,             2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl,             3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-4-yl,             3,4-dihydrooxazol-5-yl, 2,3-dihydrothiazol-2-yl,             2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl,             3,4-dihydrothiazol-2-yl, 3,4-dihydrothiazol-4-yl,             3,4-dihydrothiazol-5-yl;         -   5-membered partially unsaturated heterocyclyl attached via a             nitrogen atom:         -   4,5-dihydropyrrol-1-yl, 2,5-dihydropyrrol-1-yl,             4,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-1-yl,             4,5-dihydroisothiazol-1-yl, 2,3-dihydroisothiazol-1-yl,             2,3-dihydropyrazol-1-yl, 2,3-dihydropyrozol-2-yl,             4,5-dihydropyrazol-1-yl, 3,4-dihydropyrazol-1-yl,             2,3-dihydroimidazol-1-yl, 2,3-dihydroimidozol-3-yl,             4,5-dihydroimidazol-1-yl, 2,5-dihydroimidazol-1-yl,             2,3-dihydrooxazol-3-yl, 3,4-dihydrooxazol-3-yl,             2,3-dihydrothiazol-3-yl, 3,4-dihydrothiazol-3-yl;         -   6-membered saturated heterocyclyl attached via a carbon             atom:         -   2-piperidinyl, 3-piperidinyl, 4-piperidinyl,             1,3-dioxan-5-yl, 1,3-dithian-5-yl, 2-tetrahydropyranyl,             4-tetrahydropyranyl, 2-tetrahydrothiopyranyl,             4-tetrahydrothiopyranyl, 3-hexahydropyridazinyl,             4-hexahydropyridazinyl, 2-hexahydropyrimidinyl,             4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl,             2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl,             1,2,4-hexahydrotriazin-3-yl, tetrahydro-1,3-oxazin-2-yl,             tetrahydro-1,3-oxazin-6-yl, 2-morpholinyl, 3-morpholinyl;         -   6-membered saturated heterocyclyl attached via a nitrogen             atom:         -   1-piperidinyl, 1-hexahydropyridazinyl,             1-hexahydropyrimidinyl, 1-piperazinyl,             1,3,5-hexahydrotriazin-1-yl, 1,2,4-hexahydrotriazin-1-yl,             tetrahydro-1,3-oxazin-1-yl, 1-morpholinyl;         -   6-membered partially unsaturated heterocyclyl attached via a             carbon atom:         -   2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl,             2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl,             2H-thiopyran-4-yl, 2H-thiopyran-5-yl, 2H-thiopyran-6-yl,             5,6-dihydro-4H-1,3-oxazin-2-yl;     -   C₂-C₆-alkenyl: for example ethenyl, 1-propenyl, 2-propenyl,         1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,         1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,         2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl,         4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,         3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,         3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl,         3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,         1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl,         1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl,         3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl,         2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl,         1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl,         4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl,         3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl,         2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl,         1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,         1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl,         1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl,         1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,         2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,         2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl,         3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,         1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,         2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,         1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,         1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;     -   C₂-C₈-alkenyl: C₂-C₆-alkenyl as mentioned above, and also, for         example, 1-heptenyl, 2-heptenyl, 3-heptenyl, 2-methyl-1-hexenyl,         2-methyl-2-hexenyl, 2-methyl-3-hexenyl, 2-methyl-4-hexenyl,         2-methyl-5-hexenyl, 3-methyl-1-hexenyl, 3-methyl-2-hexenyl,         3-methyl-3-hexenyl, 3-methyl-4-hexenyl, 3-methyl-5-hexenyl,         2,2-dimethyl-3-pentenyl, 2,2-dimethyl-4-pentenyl,         2,3-dimethyl-1-pentenyl, 2,3-dimethyl-2-pentenyl,         2,3-dimethyl-3-pentenyl, 2,3-dimethyl-4-pentenyl,         2,4-dimethyl-1-pentenyl, 2,4-dimethyl-2-pentenyl,         3,3-dimethyl-1-pentenyl, 2,2-dimethyl-3-methyl-3-butenyl,         1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl, 2-methyl-1-heptenyl,         2-methyl-2-heptenyl, 2-methyl-3-heptenyl, 2-methyl-4-heptenyl,         2-methyl-5-heptenyl, 2-methyl-6-heptenyl, 3-methyl-1-heptenyl,         3-methyl-2-heptenyl, 3-methyl-3-heptenyl, 3-methyl-4-heptenyl,         3-methyl-5-heptenyl, 3-methyl-6-heptenyl, 4-methyl-1-heptenyl,         4-methyl-2-heptenyl, 4-methyl-3-heptenyl,         2,2-dimethyl-3-hexenyl, 2,2-dimethyl-4-hexenyl,         2,2-dimethyl-5-hexenyl, 2,3-dimethyl-1-hexenyl,         2,3-dimethyl-2-hexenyl, 2,3-dimethyl-3-hexenyl,         2,3-dimethyl-4-hexenyl, 2,3-dimethyl-5-hexenyl,         2,4-dimethyl-1-hexenyl, 2,4-dimethyl-2-hexenyl,         2,4-dimethyl-3-hexenyl, 2,4-dimethyl-4-hexenyl,         2,4-dimethyl-5-hexenyl, 3,3-dimethyl-1-hexenyl,         3,3-dimethyl-4-hexenyl, 3,3-dimethyl-5-hexenyl,         2,2,3-trimethyl-3-pentyl, 2,2,3-trimethyl-4-pentyl,         2,3,3-trimethyl-1-pentyl, 2,3,3-trimethyl-4-pentyl,         2,3,4-trimethyl-1-pentyl and 2,3,4-trimethyl-2-pentyl;     -   C₂-C₆-alkynyl: for example ethynyl, 1-propynyl, 2-propynyl,         1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl,         1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl,         1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl,         3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl,         1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl,         1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl,         2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl,         3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl,         1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl,         1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl,         3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl,         2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;     -   C₂-C₈-alkynyl: C₂-C₆-alkynyl as mentioned above, and also, for         example, 1-heptynyl, 2-heptynyl, 3-heptynyl, 2-methyl-3-hexynyl,         2-methyl-4-hexynyl, 2-methyl-5-hexynyl, 3-methyl-1-hexynyl,         3-methyl-4-hexynyl, 3-methyl-5-hexynyl, 2,2-dimethyl-3-pentynyl,         2,2-dimethyl-4-pentynyl, 2,3-dimethyl-4-pentynyl,         3,3-dimethyl-1-pentynyl, 1-octynyl, 2-octynyl, 3-octynyl,         4-octynyl, 2-methyl-3-heptynyl, 2-methyl-4-heptynyl,         2-methyl-5-heptynyl, 2-methyl-6-heptynyl, 3-methyl-1-heptynyl,         3-methyl-4-heptynyl, 3-methyl-5-heptynyl, 3-methyl-6-heptynyl,         4-methyl-1-heptynyl, 4-methyl-2-heptynyl,         2,2-dimethyl-3-hexynyl, 2,2-dimethyl-4-hexynyl,         2,2-dimethyl-5-hexynyl, 2,3-dimethyl-4-hexynyl,         2,3-dimethyl-5-hexynyl, 2,4-dimethyl-5-hexynyl,         3,3-dimethyl-1-hexynyl, 3,3-dimethyl-4-hexynyl,         3,3-dimethyl-5-hexynyl, 2,2,3-trimethyl-4-pentynyl and         2,3,3-trimethyl-4-pentynyl;     -   C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which         is partially or fully substituted by fluorine, chlorine, bromine         and/or iodine, i.e., for example, chloromethyl, dichloromethyl,         trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,         chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,         2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl,         2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,         2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,         2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl,         3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,         2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl,         2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,         3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl,         heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl,         1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl,         4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl;     -   C₁-C₆-haloalkyl: C₁-C₄-haloalkyl as mentioned above, and also,         for example 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl,         5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl,         6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;     -   C₁-C₈-haloalyl: C₁-C₆-haloalyl as mentioned above, and also, for         example, 7-fluoroheptyl, 7-chloroheptyl, 7-bromoheptyl,         7-iodoheptyl, perfluoroheptyl, 8-fluorooctyl, 8-chlorooctyl,         8-bromooctyl, 8-iodooctyl and heptadecafluorooctyl;     -   C₂-C₆-haloalkenyl: a C₂-C₆-alkenyl radical as mentioned above         which is partially or fully substituted by fluorine, chlorine,         bromine and/or iodine, for example 2-chlorovinyl, 2-chloroallyl,         3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl,         2,3,3-trichloroallyl, 2,3-dichloro-2-butenyl, 2-bromovinyl,         2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl,         2,3,3-tribromoallyl and 2,3-dibromo-2-butenyl;     -   C₂-C₈-haloalkenyl: a C₁-C₆-haloalkenyl radical as mentioned         above, and also, for example, 2-chloro-1-heptenyl,         3-chloro-1-heptenyl, 2,3-dichloro-1-heptenyl,         3,3-dichloro-1-heptenyl, 2,3,3-trichloro-1-heptenyl,         2-bromo-1-heptenyl, 3-bromo-1-heptenyl, 2,3-dibromo-1-heptenyl,         3,3-dibromo-1-heptenyl, 2,3,3-tribromo-1-heptenyl,         2-chloro-1-octenyl, 3-chloro-1-octenyl, 2,3-dichloro-1-octenyl,         3,3-dichloro-1-octenyl, 2,3,3-trichloro-1-octenyl,         2-bromo-1-octenyl, 3-bromo-1-octenyl, 2,3-dibromo-1-octenyl,         3,3-dibromo-1-octenyl and 2,3,3-tribromo-1-octenyl;     -   C₂-C₆-haloalkynyl: a C₂-C₆-alkynyl radical as mentioned above         which is partially or fully substituted by fluorine, chlorine,         bromine and/or iodine, for example 1,1-difluoroprop-2-yn-1-yl,         3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl,         4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl,         4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl,         5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl and         6-iodohex-5-yn-1-yl;     -   C₂-C₈-haloalkynyl: a C₁-C₆-haloalkynyl radical as mentioned         above, and also, for example, 7-fluorohept-5-yn-1-yl,         7-iodohept-6-yn-1-yl, 8-fluorooct-6-yn-1-yl and         8-iodooct-7-yn-1-yl;     -   C₁-C₄-cyanoalkyl: for example cyanomethyl, 1-cyanoethyl,         1-cyanopropyl, 2-cyanopropyl, 3-cyanopropyl, 1-cyanoprop-2-yl,         2-cyanoprop-2-yl, 1-cyanobutyl, 2-cyanobutyl, 3-cyanobutyl,         4-cyanobutyl, 1-cyanobut-2-yl, 2-cyanobut-2-yl, 1-cyanobut-3-yl,         2-cyanobut-3-yl, 1-cyano-2-methylprop-3-yl,         2-cyano-2-methylprop-3-yl, 3-cyano-2-methylprop-3-yl or         2-cyanomethylprop-2-yl;     -   C₁-C₆-cyanoalkyl: C₁-C₄-cyanoalkyl as mentioned above, and also,         for example, 5-cyanopentyl or 6-cyanohexyl;     -   C₁-C₈-cyanoalkyl: C₁-C₆-cyanoalkyl as mentioned above, and also,         for example, 7-cyanoheptyl or 8-cyanooctyl;     -   C₂-C₆-cyanoalkenyl: a C₂-C₆-alkenyl radical as mentioned above         which is substituted by cyano, for example 2-cyanovinyl,         2-cyanoallyl, 3-cyanoallyl, 2-cyanobut-2-enyl or         3-cyanobut-2-enyl;     -   C₂-C₈-cyanoalkenyl: a C₂-C₆-cyanoalkenyl radical as mentioned         above, and also, for example, 2-cyano-1-heptenyl,         3-cyano-1-heptenyl, 2-cyano-1-octenyl or 3-cyano-1-octenyl;     -   C₁-C₄-alkoxy and the alkoxy moieties of         C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,         C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,         C₁-C₄-alkoxycarbonylamino,         N—C₁-C₄-alkoxycarbonyl-N—C₁-C₄-alkylamino,         C₁-C₄-Alkoxycarbonyl(C₁-C₄)alkoxy and phenyl-C₁-C₄-alkoxy: for         example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy,         1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;     -   C₁-C₆-alkoxy: C₁-C₄-alkoxy as mentioned above, and the alkoxy         moieties of C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkoxy,         C₁-C₆-alkoxycarbonyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl,         C₁-C₆-alkoxycarbonylamino,         N—C₁-C₆-alkoxycarbonyl-N—C₁-C₆-alkylamino,         C₁-C₆-alkoxycarbonyl(C₁-C₆)alkoxy and phenyl-C₁-C₆-alkoxy, for         example, pentoxy, 1-methylbutoxy, 2-methylbutoxy,         3-methoxylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy,         2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy,         2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,         1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,         2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,         1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,         1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and         1-ethyl-2-methylpropoxy;     -   C₁-C₈-alkoxy: C₁-C₆-alkoxy as mentioned above, and the alkoxy         moieties of C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkoxy-C₁-C₈-alkoxy,         C₁-C₈-alkoxycarbonyl, C₁-C₈-alkoxycarbonyl-C₁-C₈-alkyl,         C₁-C₈-alkoxycarbonylamino,         N—C₁-C₈-alkoxycarbonyl-N—C₁-C₈-alkylamino and         phenyl-C₁-C₈-alkoxy, for example, heptoxy, 2-methylhexoxy,         3-methylhexoxy, 2,2-dimethylpentoxy, 2,3-dimethylpentoxy,         2,4-dimethylpentoxy, 3,3-dimethylpentoxy,         2,2-dimethyl-3-methylbutoxy, octoxy, 2-methylheptoxy,         3-methylheptoxy, 4-methylheptoxy, 2,2-dimethylhexoxy,         2,3-dimethylhexoxy, 2,4-dimethylhexoxy, 3,3-dimethylhexoxy,         2,2-dimethyl-3-methylpentoxy, 2-methyl-3,3-dimethylpentoxy,         2,3,4-trimethylpentoxy and 2,2,3,3-tetramethylbutoxy;     -   C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above         which is partially or fully substituted by fluorine, chlorine,         bromine and/or iodine, i.e., for example, fluoromethoxy,         difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy,         bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy,         2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,         2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,         2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,         2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,         3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,         2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy,         2,3-difluoropropoxy, 2,3-dichloropropoxy,         3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,         2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy,         1-(fluoromethyl)-2-fluoroethoxy,         1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy,         4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and         nonafluorobutoxy;     -   C₁-C₆-haloalkoxy: C₁-C₄-haloalkoxy as mentioned above, and also,         for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy,         5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy,         6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and         dodecafluorohexoxy;     -   C₁-C₈-haloalkoxy: C₁-C₆-haloalkoxy as mentioned above, and also,         for example, 7-fluoroheptoxy, 7-chloroheptoxy, 7-bromoheptoxy,         7-iodoheptoxy, perfluoroheptoxy, 8-fluorooctoxy, 8-chlorooctoxy,         8-bromooctoxy, 8-iodooctoxy and heptadecafluorooctoxy;     -   C₁-C₆-alkylamino and the alkylamino moieties of         C₁-C₆-alkylamino-C₁-C₆-alkyl,         N—C₁-C₆-alkylcarbonyl-N-C₁-C₆-alkylamino,         C₁-C₆-alkylaminocarbonyl and         C₁-C₆-alkylaminocarbonyl-C₁-C₆-alkyl, for example methylamino,         ethylamino, propylamino, 1-methylethylamino, butylamino,         1-methylpropylamino, 2-methylpropylamino,         1,1-dimethylethylamino, pentylamino, 1-methylbutylamino,         2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino,         1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino,         1,2-dimethylpropylamino, 1-methylpentylamino,         2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino,         1,1-dimethylbutylamino, 1,2-dimethylbutylamino,         1,3-dimethylbutylamino, 2,2-dimethylbutylamino,         2,3-dimethylbutylamino, 3,3-dimethylbutylamino,         1-ethylbutylamino, 2-ethylbutylamino,         1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino,         1-ethyl-1-methylpropylamino and 1-ethyl-2-methylpropylamino;     -   C₁-C₈-alkylamino: C₁-C₆-alkylamino as mentioned above, and the         alkylamino moieties of C₁-C₈-alkylamino-C₁-C₈-alkyl,         N—C₁-C₈-alkylcarbonyl-N—C₁-C₈-alkylamino,         N—C₁-C₈-alkoxycarbonyl-N—C₁-C₈-alkylamino,         C₁-C₈-alkylaminocarbonyl and         C₁-C₈-alkylaminocarbonyl-C₁-C₈-alkyl: for example, heptylamino,         2-methylhexylamino, 3-methylhexylamino, 2,2-dimethylpentylamino,         2,3-dimethylpentylamino, 2,4-dimethylpentylamino,         3,3-dimethylpentylamino, 2,2-dimethyl-3-methylbutylamino,         octylamino, 2-methylheptylamino, 3-methylheptylamino,         4-methylheptylamino, 2,2-dimethylhexylamino,         2,3-dimethylhexylamino, 2,4-dimethylhexylamino,         3,3-dimethylhexylamino, 2,2-dimethyl-3-methylpentylamino,         2-methyl-3,3-dimethylpentylamino, 2,3,4-trimethylpentylamino and         2,2,3,3-tetramethylbutylamino;     -   di(C₁-C₄-alkyl)amino and the dialkylamino moieties of         di(C₁-C₄-alkyl)amino-C₁-C₄-alkyl, di(C₁-C₄-alkyl)aminocarbonyl         and di(C₁-C₄-alkyl)aminocarbonyl-C₁-C₄-alkyl: for example         N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino,         N,N-di(1-methylethyl)amino, N,N-dibutylamino,         N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino,         N,N-di(1,1-dimethylethyl)amino, N-ethyl-N-methylamino,         N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino,         N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino,         N-methyl-N-(2-methylpropyl)amino,         N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino,         N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino,         N-ethyl-N-(1-methylpropyl)amino,         N-ethyl-N-(2-methylpropyl)amino,         N-ethyl-N-(1,1-dimethylethyl)amino,         N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino,         N-(1-methylpropyl)-N-propylamino,         N-(2-methylpropyl)-N-propylamino,         N-(1,1-dimethylethyl)-N-propylamino,         N-butyl-N-(1-methylethyl)amino,         N-(1-methylethyl)-N-(1-methylpropyl)amino,         N-(1-methylethyl)-N-(2-methylpropyl)amino,         N-(1,1-dimethylethyl)-N-(1-methylethyl)amino,         N-butyl-N-(1-methylpropyl)amino,         N-butyl-N-(2-methylpropyl)amino,         N-butyl-N-(1,1-dimethylethyl)amino,         N-(1-methylpropyl)-N-(2-methylpropyl)amino,         N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino and         N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;     -   di(C₁-C₆-alkyl)amino: di(C₁-C₄-alkyl)amino as mentioned above,         and the dialkylamino moieties of         di(C₁-C₆-alkyl)amino-C₁-C₆-alkyl, di(C₁-C₆-alkyl)aminocarbonyl         and di(C₁-C₆-alkyl)aminocarbonyl-C₁-C₆-alkyl: for example,         N,N-dipentylamino, N,N-dihexylamino, N-methyl-N-pentylamino,         N-ethyl-N-pentylamino, N-methyl-N-hexylamino and         N-ethyl-N-hexylamino;     -   di(C₁-C₈-alkyl)amino: di(C₁-C₆-alkyl)amino as mentioned above,         and the dialkylamino moieties of         di(C₁-C₈-alkyl)amino-C₁-C₈-alkyl, di(C₁-C₈-alkyl)aminocarbonyl         and di(C₁-C₈-alkyl)aminocarbonyl-C₁-C₈-alkyl: for example,         N,N-diheptylamino, N,N-dioctylamino, N-methyl-N-heptylamino,         N-ethyl-N-heptylamino, N-methyl-N-octylamino and         N-ethyl-N-octylamino;     -   C₁-C₄-alkylthio and the alkylthio moieties of         C₁-C₄-alkylthio-C₁-C₄-alkyl: for example methylthio, ethylthio,         propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio,         2-methylpropylthio and 1,1-dimethylethylthio;     -   C₁-C₆-alkylthio: C₁-C₄-alkylthio as mentioned above, and the         alkylthio moieties of C₁-C₆-alkylthio-C₁-C₆-alkyl and also, for         example, pentylthio, 1-methylbutylthio, 2-methylbutylthio,         3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio,         hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio,         1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio,         4-methylpentylthio, 1,1-dimethylbutylthio,         1,2-dimethylbutylthio, 1,3-dimethylbutylthio,         2,2-dimethylbutylthio, 2,3-dimethylbutylthio,         3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio,         1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,         1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio;     -   C₁-C₈-alkylthio: C₁-C₆-alkylthio as mentioned above, and the         alkylthio moieties of C₁-C₈-alkylthio-C₁-C₈-alkyl and also, for         example, heptylthio, 2-methylhexylthio, 3-methylhexylthio,         2,2-dimethylpentylthio, 2,3-dimethylpentylthio,         2,4-dimethylpentylthio, 3,3-dimethylpentylthio,         2,2-dimethyl-3-methylbutylthio, octylthio, 2-methylheptylthio,         3-methylheptylthio 4-methylheptylthio, 2,2-dimethylhexylthio,         2,3-dimethylhexylthio, 2,4-dimethylhexylthio,         3,3-dimethylhexylthio, 2,2,3-trimethylpentylthio,         2,3,3-trimethylpentylthio, 2,3,4-trimethylpentylthio and         2,2,3,3-tetramethylbutylthio;     -   C₁-C₄-haloalkylthio: a C₁-C₄-alkylthio radical as mentioned         above which is partially or fully substituted by fluorine,         chlorine, bromine and/or iodine, i.e., for example,         fluoromethylthio, difluoromethylthio, trifluoromethylthio,         chlorodifluoromethylthio, bromodifluoromethylthio,         2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio,         2-iodoethylthio, 2,2-difluoroethylthio,         2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio,         2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,         2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio,         2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio,         3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio,         2,2-difluoropropylthio, 2,3-difluoropropylthio,         2,3-dichloropropylthio, 3,3,3-trifluoropropylthio,         3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio,         heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio,         1-(chloromethyl)-2-chloroethylthio,         1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio,         4-chlorobutylthio, 4-bromobutylthio and nonafluorobutylthio;     -   C₁-C₆-haloalkylthio: C₁-C₄-haloalkylthio as mentioned above, and         also, for example, 5-fluoropentylthio, 5-chloropentylthio,         5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio,         6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio,         6-iodohexylthio and dodecafluorohexylthio;     -   C₁-C₈-haloalkylthio: C₁-C₆-haloalkylthio as mentioned above, and         also, for example, 7-fluoroheptylthio, 7-chloroheptylthio,         7-bromoheptylthio, 7-iodoheptylthio, perfluoroheptylthio,         8-fluorooctylthio, 8-chlorooctylthio, 8-bromooctylthio,         8-iodooctylthio and heptadecafluorooctylthio;     -   C₁-C₆-alkylsulfinyl (C₁-C₆-alkyl-S(═O)—): for example         methylsulfinyl, ethylsulfinyl, propylsulfinyl,         1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl,         2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl,         pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl,         3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl,         1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl,         1,2-dimethylpropylsulfinyl, hexylsulfinyl,         1-methylpentylsulfinyl, 2-methylpentylsulfinyl,         3-methylpentylsulfinyl, 4-methylpentylsulfinyl,         1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl,         1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl,         2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl,         1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,         1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,         1-ethyl-1-methylpropylsulfinyl and         1-ethyl-2-methylpropylsulfinyl;     -   C₁-C₈-alkylsulfinyl (C₁-C₈-alkyl-S(═O)—): C₁-C₆-alkylsulfinyl as         mentioned above, and also, for example, heptylsulfinyl,         2-methylhexylsulfinyl, 3-methylhexylsulfinyl,         2,2-dimethylpentylsulfinyl, 2,3-dimethylpentylsulfinyl,         2,4-dimethylpentylsulfinyl, 3,3-dimethylpentylsulfinyl,         2,2-dimethyl-3-methylbutylsulfinyl, octylsulfinyl,         2-methylheptylsulfinyl, 3-methylheptylsulfinyl         4-methylheptylsulfinyl, 2,2-dimethylhexylsulfinyl,         2,3-dimethylhexylsulfinyl, 2,4-dimethylhexylsulfinyl,         3,3-dimethylhexylsulfinyl, 2,2,3-trimethylpentylsulfinyl,         2,3,3-trimethylpentylsulfinyl, 2,3,4-trimethylpentylsulfinyl and         2,2,3,3-tetramethylbutylsulfinyl;     -   C₁-C₆-haloalkylsulfinyl: C₁-C₆-alkylsulfinyl radical as         mentioned above which is partially or fully substituted by         fluorine, chlorine, bromine and/or iodine, i.e., for example,         fluoromethylsulfinyl, difluoromethylsulfinyl,         trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl,         bromodifluoromethylsulfinyl, 2-fluoroethylsulfinyl,         2-chloroethylsulfinyl, 2-bromoethylsulfinyl,         2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl,         2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl,         2-chloro-2-fluoroethylsulfinyl,         2-chloro-2,2-difluoroethylsulfinyl,         2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl,         2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl,         2-chloropropylsulfinyl, 3-chloropropylsulfinyl,         2-bromopropylsulfinyl, 3-bromopropylsulfinyl,         2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl,         2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl,         3,3,3-trichloropropylsulfinyl,         2,2,3,3,3-pentafluoropropylsulfinyl, heptafluoropropylsulfinyl,         1-(fluoromethyl)-2-fluoroethylsulfinyl,         1-(chloromethyl)-2-chloroethylsulfinyl,         1-(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl,         4-chlorobutylsulfinyl, 4-bromobutylsulfinyl,         nonafluorobutylsulfinyl, 5-fluoropentylsulfinyl,         5-chloropentylsulfinyl, 5-bromopentylsulfinyl,         5-iodopentylsulfinyl, undecafluoropentylsulfinyl,         6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl,         6-bromohexylsulfinyl, 6-iodohexylsulfinyl and         dodecafluorohexylsulfinyl;     -   C₁-C₈-haloalkylsulfinyl: C₁-C₆-haloalkylsulfinyl as mentioned         above, and also, for example 7-fluoroheptylsulfinyl,         7-chloroheptylsulfinyl, 7-bromoheptylsulfinyl,         7-iodoheptylsulfinyl, perfluoroheptylsulfinyl,         8-fluorooctylsulfinyl, 8-chlorooctylsulfinyl,         8-bromooctylsulfinyl, 8-iodooctylsulfinyl and         perfluorooctylsulfinyl;     -   C₁-C₆-alkylsulfonyl (C₁-C₆-alkyl-S(═O)₂—) and the alkylsulfonyl         moieties of C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl: for example         methylsulfonyl, ethylsulfonyl, propylsulfonyl,         1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl,         2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl,         pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl,         3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl,         1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl,         1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl,         2-methylpentylsulfonyl, 3-methylpentylsulfonyl,         4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,         1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,         2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,         3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl,         2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl,         1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl         and 1-ethyl-2-methylpropylsulfonyl;     -   C₁-C₈-alkylsulfonyl (C₁-C₈-alkyl-S(═O)₂—): C₁-C₆-alkylsulfonyl         as mentioned above, and the alkylsulfonyl moieties of         C₁-C₈-alkylsulfonyl-C₁-C₈-alkyl: for example, heptylsulfonyl,         2-methylhexylsulfonyl, 3-methylhexylsulfonyl,         2,2-dimethylpentylsulfonyl, 2,3-dimethylpentylsulfonyl,         2,4-dimethylpentylsulfonyl, 3,3-dimethylpentylsulfonyl,         2,2-dimethyl-3-methylbutylsulfonyl, octylsulfonyl,         2-methylheptylsulfonyl, 3-methylheptylsulfonyl         4-methylheptylsulfonyl, 2,2-dimethylhexylsulfonyl,         2,3-dimethylhexylsulfonyl, 2,4-dimethylhexylsulfonyl,         3,3-dimethylhexylsulfonyl, 2,2,3-trimethylpentylsulfonyl,         2,3,3-trimethylpentylsulfonyl, 2,3,4-trimethylpentylsulfonyl and         2,2,3,3-tetramethylbutylsulfonyl;     -   C₁-C₆-haloalkylsulfonyl: a C₁-C₆-alkylsulfonyl radical as         mentioned above which is partially or fully substituted by         fluorine, chlorine, bromine and/or iodine, i.e., for example,         fluoromethylsulfonyl, difluoromethylsulfonyl,         trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl,         bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl,         2-chloroethylsulfonyl, 2-bromoethylsulfonyl,         2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl,         2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl,         2-chloro-2,2-difluoroethylsulfonyl,         2,2-dichloro-2-fluoroethylsulfonyl,         2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl,         2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl,         2-chloropropylsulfonyl, 3-chloropropylsulfonyl,         2-bromopropylsulfonyl, 3-bromopropylsulfonyl,         2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,         2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl,         3,3,3-trichloropropylsulfonyl,         2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl,         1-(fluoromethyl)-2-fluoroethylsulfonyl,         1-(chloromethyl)-2-chloroethylsulfonyl,         1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl,         4-chlorobutylsulfonyl, 4-bromobutylsulfonyl,         nonafluorobutylsulfonyl, 5-fluoropentylsulfonyl,         5-chloropentylsulfonyl, 5-bromopentylsulfonyl,         5-iodopentylsulfonyl, 6-fluorohexylsulfonyl,         6-bromohexylsulfonyl, 6-iodohexylsulfonyl and         dodecafluorohexylsulfonyl;     -   C₁-C₈-haloalkylsulfonyl: C₁-C₆-haloalkylsulfonyl as mentioned         above, and also, for example, 7-fluoroheptylsulfonyl,         7-chloroheptylsulfonyl, 7-bromoheptylsulfonyl,         7-iodoheptylsulfonyl, perfluoroheptylsulfonyl,         8-fluorooctylsulfonyl, 8-chlorooctylsulfonyl,         8-bromooctylsulfonyl, 8-iodooctylsulfonyl and         heptadecafluorooctylsulfonyl;     -   aryl: a mono- to trinuclear aromatic carbocycle having 6 to 14         ring members, such as, for example, phenyl, naphthyl,         anthracenyl and phenanthrenyl;     -   5-membered heteroaryl having one to four nitrogen atoms, or         having one to three nitrogen atoms and one oxygen or sulfur atom         or having one oxygen or sulfur atom is carbon atom-attached         aromatic 5-membered heterocycles which, in addition to carbon         atoms, may contain one to four nitrogen atoms or one to three         nitrogen atoms and one sulfur or oxygen atom or one oxygen or         one sulfur atom as ring members,         -   for example aromatic 5-membered heterocycles which are             attached via a carbon atom and contain one heteroatom, such             as, for example, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl,             2-pyrrolyl, 3-pyrrolyl;         -   for example aromatic 5-membered heterocycles which are             attached via a carbon atom and contain two heteroatoms, such             as, for example, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl,             3-isothiazolyi, 4-isothiazolyl, 5-isothiazolyl, 2-oxazolyl,             4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl,             5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 3-pyrazolyl,             4-pyrazolyl, 5-pyrazolyl;         -   for example aromatic 5-membered heterocycles which are             attached via a carbon atom and contain three heteroatoms,             for example 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl,             1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,             1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, tetrazol-2-yl;         -   for example aromatic 5-membered heterocycles which are             attached via a carbon atom and contain four heteroatoms,             such as, for example, tetrazol-2-yl;     -   6-membered heteroaryl containing one to four nitrogen atoms: for         example 6-membered heterocycles which are attached via a carbon         atom and which may, in addition to carbon atoms, contain one to         four, preferably one to three, nitrogen atoms as ring members,         for example 2-pyridinyl, 3-pyridinyl, 4-pyridinyl,         3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl,         5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl,         1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl and         1,2,4,5-tetrazinyl.

In a particular embodiment, the variables in the compounds of the formula I are as defined below, these definitions being, both on their own and in combination with one another, particular embodiments of the compounds of the formula I:

Preference is given to 3-heteroaryl-substituted isoxazolines of the formula I in which

-   X is a 6-membered heteroaryl having one to four nitrogen atoms which     is partially or fully halogenated and/or carries one to three     substituents selected from the following group:     -   cyano, nitro, hydroxyl, C₁-C₈-alkyl, C₃-C₆-cycloalkyl,         C₃-C₆-halocycloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl,         C₁-C₈-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,         C₁-C₈-alkoxy, C₁-C₈-haloalkoxy, C₁-C₈-alkoxy-C₁-C₈-alkyl, amino,         C₁-C₈-alkylamino, di(C₁-C₈-alkyl)amino, amino-C₁-C₈-alkyl,         C₁-C₈-alkylamino-C₁-C₈-alkyl, di(C₁-C₈-alkyl)amino-C₁-C₈-alkyl,         C₁-C₈-alkylthio, C₁-C₈-haloalkylthio,         C₁-C₈-alkylthio-C₁-C₈-alkyl, C₁-C₈-alkylsulfinyl,         C₁-C₈-haloalkylsulfinyl, C₁-C₈-alkylsulfonyl,         C₁-C₈-haloalkylsulfonyl, C₁-C₈-alkylsulfonyl-C₁-C₈-alkyl,         C₁-C₈-alkoxycarbonyl, C₁-C₈-alkoxycarbonyl-C₁-C₈-alkyl,         aminocarbonyl, C₁-C₈-alkylaminocarbonyl,         di(C₁-C₈-alkyl)aminocarbonyl, aminocarbonyl-C₁-C₈-alkyl,         C₁-C₈-alkylaminocarbonyl-C₁-C₈-alkyl,         di(C₁-C₈-alkyl)aminocarbonyl-C₁-C₈-alkyl, carboxyl,         carboxy-C₁-C₈-alkyl, phenyl, phenoxy, phenylthio, phenylamino,         phenyl-C₁-C₈-alkyl, phenyl-C₁-C₈-alkoxy, 3- to 6-membered         heterocyclyl and 5- to 6-membered heteroaryl, where the eight         last-mentioned radicals for their part may be partially or fully         halogenated and/or may carry one to three substituents selected         from the group consisting of nitro, cyano, C₁-C₈-alkyl,         C₁-C₈-alkoxy, C₁-C₈-haloalkyl, C₁-C₈-haloalkoxy,         C₁-C₈-alkylthio, C₁-C₈-haloalkylthio, C₁-C₈-alkylsulfinyl,         C₁-C₈-haloalkylsulfinyl, C₁-C₈-alkylsulfonyl, and         C₁-C₈-haloalkylsulfonyl;     -   particular preference is given to 6-membered heteroaryl         containing one to four nitrogen atoms which is partially or         fully halogenated and/or carries one to three substituents         selected from the following group:     -   cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,         C₃-C₆-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,         C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, amino,         C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, amino-C₁-C₆-alkyl,         C₁-C₆-alkylamino-C₁-C₆-alkyl, di(C₁-C₆-alkyl)amino-C₁-C₆-alkyl,         C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,         C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkylsulfinyl,         C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl,         C₁-C₆-alkoxycarbonyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl,         aminocarbonyl, C₁-C₆-alkylaminocarbonyl,         di(C₁-C₆-alkyl)aminocarbonyl, aminocarbonyl-C₁-C₆-alkyl,         C₁-C₆-alkylaminocarbonyl-C₁-C₆-alkyl,         di(C₁-C₆-alkyl)aminocarbonyl-C₁-C₆-alkyl, carboxyl and         carboxy-C₁-C₆-alkyl;     -   especially preferred is 6-membered heteroaryl containing one to         four nitrogen atoms which is partially or fully halogenated         and/or carries one to three substituents selected from the         following group:     -   cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,         C₃-C₆-halocycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,         C₁-C₆-haloalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, amino,         C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,         C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,         C₁-C₆-alkoxycarbonyl, aminocarbonyl, C₁-C₆-alkylaminocarbonyl,         di(C₁-C₆-alkyl)aminocarbonyl, carboxyl and carboxy-C₁-C₆-alkyl.     -   very particular preference is given to 6-membered heteroaryl         containing one to four nitrogen atoms which is partially         halogenated and/or carries one or two substituents selected from         the following group:     -   cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,         C₃-C₆-halocycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,         C₁-C₆-haloalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, amino,         C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,         C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,         C₁-C₆-alkoxycarbonyl, aminocarbonyl, C₁-C₆-alkylaminocarbonyl,         di(C₁-C₆-alkyl)aminocarbonyl, carboxyl and carboxy-C₁-C₆-alkyl;     -   most preference is given to 6-membered heteroaryl containing one         to four nitrogen atoms which is partially halogenated and/or         carries one substituent selected from the following group:     -   cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,         C₃-C₆-halocycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,         C₁-C₆-haloalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, amino,         C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,         C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,         C₁-C₆-alkoxycarbonyl, aminocarbonyl, C₁-C₆-alkylaminocarbonyl,         di(C₁-C₆-alkyl)aminocarbonyl, carboxyl and carboxy-C₁-C₆-alkyl.

Preference is also given to the 3-heteroaryl-substituted isoxazolines of the formula I in which

-   X is 6-membered heteroaryl containing one to three nitrogen atoms,     -   preferably 6-membered heteroaryl containing one or two nitrogen         atoms,     -   in particular pyridyl, pyrimidyl or pyrazinyl, very preferably         pyridyl or pyrimidyl;     -   likewise very preferably pyridyl or pyrazinyl, very preferably         pyridyl; and     -   the 6-membered heteroaryl is substituted as described above;     -   extraordinary preference is given to 6-membered heteroaryl         having one or two nitrogen atoms,     -   in particular pyridyl or pyrazinyl, very preferably pyridyl; and     -   the 6-membered heteroaryl is substituted as described above; and     -   the 6-membered heteroaryl is attached to the isoxazoline         skeleton in a position ortho or meta to a nitrogen.

Preference is also given to the 3-heteroaryl-substituted isoxazolines of the formula I in which

-   X is 6-membered heteroaryl containing one or two nitrogen atoms     which is partially or fully halogenated and/or carries one or two     substituents selected from the following group:     -   cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,         amino, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,         C₁-C₆-alkylsulfinyl and C₁-C₆-alkylsulfonyl; preferably cyano,         nitro, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,         C₁-C₆-haloalkoxy, amino, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino,         C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl and C₁-C₆-alkylsulfonyl;         and     -   which is attached to the isoxazoline skeleton in a position         ortho or meta to a nitrogen of the 6-membered heteroaryl;     -   preferably 6-membered heteroaryl containing one or two nitrogen         atoms which is partially halogenated and/or carries, in a         position ortho to a nitrogen atom, one or two substituents         selected from the following group:     -   cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,         amino, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio         and C₁-C₆-alkylsulfinyl;     -   preferably cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino, C₁-C₆-alkylamino,         di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio and C₁-C₆-alkylsulfinyl;         and     -   is attached to the isoxazoline skeleton in a position ortho or         meta to a nitrogen of the 6-membered heteroaryl;     -   especially preferably 6-membered heteroaryl containing one or         two nitrogen atoms which is partially halogenated and/or         carries, in a position ortho to a nitrogen atom, one substituent         selected from the following group:     -   cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,         C₂-C₆-alkynyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy and         C₁-C₆-haloalkoxy;     -   preferably C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and         C₁-C₆-haloalkoxy; and     -   is attached to the isoxazoline skeleton in a position ortho or         meta to a nitrogen of the 6-membered heteroaryl.

Preference is also given to the 3-heteroaryl-substituted isoxazolines of the formula I, in which

-   X is 6-membered heteroaryl containing one or two nitrogen atoms     which is partially or fully halogenated and/or carries one or two     substituents selected from the following group:     -   cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl and         C₂-C₆-alkynyl; and     -   which is attached to the isoxazoline skeleton in a position         ortho or meta to a nitrogen of the 6-membered heteroaryl;     -   preferably 6-membered heteroaryl containing one or two nitrogen         atoms which is partially halogenated and/or carries, in the         position ortho to a nitrogen atom, one or two substituents         selected from the following group:     -   cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl and         C₂-C₄-alkynyl; and     -   is attached to the isoxazoline skeleton in a position ortho or         meta to a nitrogen of the 6-membered heteroaryl;     -   especially preferably 6-membered heteroaryl containing one or         two nitrogen atoms which carries, in a position ortho to a         nitrogen atom, one substituent selected from the following         group: CN, NO₂, halogen, such as, for example, fluorine,         chlorine, bromine, C₁-C₄-alkyl, such as, for example, methyl,         ethyl, isopropyl, C₁-C₄-haloalkyl, such as, for example,         trifluoromethyl, C₂-C₄-alkenyl, such as, for example, ethenyl,         and C₂-C₄-alkynyl, such as, for example, ethynyl; and is         attached to the isoxazoline skeleton in a position ortho or meta         to a nitrogen of the 6-membered heteroaryl;     -   with extraordinary preference 6-membered heteroaryl containing         one or two nitrogen atoms which carries, in a position ortho to         a nitrogen atom, one substituent selected from the following         group: F, Cl, Br, CN, CH₃, C₂H₅, iC₃H₇, CF₃, ethenyl and         ethynyl; and is attached to the isoxazoline skeleton in a         position ortho or meta to a nitrogen of the 6-membered         heteroaryl.

Preference is also given to the 3-heteroaryl-substituted isoxazolines of the formula I in which

-   X is a 5-membered heteroaryl having one to four nitrogen atoms or     one to three nitrogen atoms and one sulfur or oxygen atom or one     oxygen or sulfur atom, selected from the following group: pyrrolyl,     furanyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,     1,2,3-triazolyl, 1H-1,2,4-triazolyl, 4H-1,2,4-triazolyl,     1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl,     1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl and     1H-tetrazolyl;     -   is partially or fully halogenated and/or carries one to three         substituents selected from the following group:     -   cyano, nitro, hydroxyl, C₁-C₈-alkyl, C₃-C₆-cycloalkyl,         C₃-C₆-halocycloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl,         C₁-C₈-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,         C₁-C₈-alkoxy, C₁-C₈-haloalkoxy, C₁-C₈-alkoxy-C₁-C₈-alkyl, amino,         C₁-C₈-alkylamino, di(C₁-C₈-alkyl)amino, amino-C₁-C₈-alkyl,         C₁-C₈-alkylamino-C₁-C₈-alkyl, di(C₁-C₈-alkyl)amino-C₁-C₈-alkyl,         C₁-C₈-alkylthio, C₁-C₈-haloalkylthio,         C₁-C₈-alkylthio-C₁-C₈-alkyl, C₁-C₈-alkylsulfinyl,         C₁-C₈-haloalkylsulfinyl, C₁-C₈-alkylsulfonyl,         C₁-C₈-haloalkylsulfonyl, C₁-C₈-alkylsulfonyl-C₁-C₈-alkyl,         C₁-C₈-alkoxycarbonyl, C₁-C₈-alkoxycarbonyl-C₁-C₈-alkyl,         aminocarbonyl, C₁-C₈-alkylaminocarbonyl,         di(C₁-C₈-alkyl)aminocarbonyl, aminocarbonyl-C₁-C₈-alkyl,         C₁-C₈-alkylaminocarbonyl-C₁-C₈-alkyl,         di(C₁-C₈-alkyl)aminocarbonyl-C₁-C₈-alkyl, carboxyl,         carboxy-C₁-C₈-alkyl,     -   phenyl, phenoxy, phenylthio, phenylamino, phenyl-C₁-C₈-alkyl,         phenyl-C₁-C₈-alkoxy, 3- to 6-membered heterocyclyl or 5- or         6-membered heteroaryl, where the eight last-mentioned radicals         for their part may be partially or fully halogenated and/or may         carry one to three substituents selected from the group         consisting of nitro, cyano, C₁-C₈-alkyl, C₁-C₈-alkoxy,         C₁-C₈-haloalkyl, C₁-C₈-haloalkoxy, C₁-C₈-alkylthio,         C₁-C₈-haloalkylthio, C₁-C₈-alkylsulfinyl,         C₁-C₈-haloalkylsulfinyl, C₁-C₈-alkylsulfonyl and         C₁-C₈-haloalkylsulfonyl;     -   particular preference is given to 5-membered heteroaryl         containing one to four nitrogen atoms or one to three nitrogen         atoms and one oxygen or sulfur atom or one oxygen or sulfur atom         from the following group: pyrrolyl, furanyl, imidazolyl,         oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-triazolyl,         1H-1,2,4-triazolyl, 4H-1,2,4-triazolyl, 1,2,3-oxadiazolyl,         1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl,         1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl and 1H-tetrazolyl;     -   where the 5-membered heteroaryl is partially or fully         halogenated and/or carries one to three substituents selected         from the following group:     -   cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,         C₃-C₆-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,         C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, amino,         C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, amino-C₁-C₆-alkyl,         C₁-C₆-alkylamino-C₁-C₆-alkyl, di(C₁-C₆-alkyl)amino-C₁-C₆-alkyl,         C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,         C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkylsulfinyl,         C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl,         C₁-C₆-alkoxycarbonyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl,         aminocarbonyl, C₁-C₆-alkylaminocarbonyl,         di(C₁-C₆-alkyl)aminocarbonyl, aminocarbonyl-C₁-C₆-alkyl,         C₁-C₆-alkylaminocarbonyl-C₁-C₆-alkyl,         di(C₁-C₆-alkyl)aminocarbonyl-C₁-C₆-alkyl, carboxyl and         carboxy-C₁-C₆-alkyl;     -   especially preferred is 5-membered heteroaryl containing one to         four nitrogen atoms or one to three nitrogen atoms and one         oxygen or sulfur atom or one oxygen or sulfur atom from the         following group: pyrrolyl, furanyl, imidazolyl, oxazolyl,         isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-triazolyl,         1H-1,2,4-triazolyl, 4H-1,2,4-triazolyl, 1,2,3-oxadiazolyl,         1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl,         1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl and 1H-tetrazolyl, where         the 5-membered heteroaryl is partially or fully halogenated         and/or carries one to three substituents selected from the         following group:     -   cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,         C₃-C₆-halocycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,         C₁-C₆-haloalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, amino,         C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,         C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,         C₁-C₆-alkoxycarbonyl, aminocarbonyl, C₁-C₆-alkylaminocarbonyl,         di(C₁-C₆-alkyl)aminocarbonyl, carboxyl and carboxy-C₁-C₆-alkyl;     -   very particular preference is given to 5-membered heteroaryl         containing one to four nitrogen atoms or one to three atoms and         one oxygen or sulfur atom or one oxygen or sulfur atom from the         following group: pyrrolyl, furanyl, imidazolyl, oxazolyl,         isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-triazolyl,         1H-1,2,4-triazolyl, 4H-1,2,4-triazolyl, 1,2,3-oxadiazolyl,         1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl,         1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl and 1H-tetrazolyl;     -   where the 5-membered heteroaryl is partially halogenated and/or         carries one or two substituents selected from the following         group:     -   cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,         C₃-C₆-halocycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,         C₁-C₆-haloalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, amino,         C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,         C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,         C₁-C₆-alkoxycarbonyl, aminocarbonyl, C₁-C₆-alkylaminocarbonyl,         di(C₁-C₆-alkyl)aminocarbonyl, carboxyl and carboxy-C₁-C₆-alkyl;     -   most preference is given to 5-membered heteroaryl containing one         to four nitrogen atoms or one to three nitrogen atoms and one         oxygen or sulfur atom or one oxygen or sulfur atom from the         following group:     -   pyrrolyl, furanyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl,         isothiazolyl, 1,2,3-triazolyl, 1H-1,2,4-triazolyl,         4H-1,2,4-triazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl,         1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl,         1,3,4-thiadiazolyl and 1H-tetrazolyl, where the 5-membered         heteroaryl is partially halogenated and/or carries one         substituent selected from the following group:     -   cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,         C₃-C₆-halocycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,         C₁-C₆-haloalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, amino,         C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,         C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,         C₁-C₆-alkoxycarbonyl, aminocarbonyl, C₁-C₆-alkylaminocarbonyl,         di(C₁-C₆-alkyl)aminocarbonyl, carboxyl and carboxy-C₁-C₆-alkyl.

Preference is also given to 3-heteroaryl-substituted isoxazolines of the formula I in which

-   X is 5-membered heteroaryl containing one to three nitrogen atoms or     one or two nitrogen atoms and one oxygen or sulfur atom or one     oxygen or sulfur atom, selected from the group consisting of X¹ to     X⁶

-   -   where A in X¹ to X⁴ is NR^(d), O or S,

-   -   where A is NR^(d) or O, and

-   -   where A is O or S, and

-   R^(a) is halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,     C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₆-haloalkyl,     C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, amino,     C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,     C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,     C₁-C₆-alkoxycarbonyl, aminocarbonyl, C₁-C₆-alkylaminocarbonyl,     di(C₁-C₆-alkyl)aminocarbonyl, carboxyl or carboxy-C₁-C₆-alkyl;

-   R^(b), R^(c) are hydrogen or one of the substituents mentioned under     R^(a); and

-   R^(d) is hydrogen or C₁-C₆-alkyl.

Particular preference is given to the 3-heteroaryl-substituted isoxazolines of the formula I in which

-   X is X¹, where -   R^(a) is halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino,     C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,     C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl, -   R^(b) is hydrogen or one of the substituents mentioned above under     R^(a); and -   R^(d) is hydrogen or C₁-C₆-alkyl;     -   preferably hydrogen or C₁-C₄-alkyl;         with particular preference -   X is X¹, where -   R^(a) is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or     C₁-C₆-haloalkoxy; -   R^(b) is hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,     C₁-C₆-alkoxy or C₁-C₆-haloalkoxy; and -   R^(d) is hydrogen or C₁-C₄-alkyl.

Particular preference is also given to the 3-heteroaryl-substituted isoxazolines of the formula I in which

-   X is X⁵, where -   R^(a) is halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino,     C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,     C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl; -   R^(b), R^(c) are hydrogen or one of the substituents mentioned above     under R^(a); and -   R^(d) is hydrogen or C₁-C₆-alkyl,     -   preferably hydrogen or C₁-C₄-alkyl;         preferably -   X is X⁵, where -   R^(a) is halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino,     C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,     C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl; -   R^(b), R^(c) are hydrogen or one of the substituents mentioned above     under R^(a); and -   R^(d) is hydrogen or C₁-C₄-alkyl;     where the 5-membered heterocycle is attached to the isoxazoline     skeleton in the position ortho to the heteroatom;     with particular preference -   X is X⁵, where -   R^(a) is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or     C₁-C₆-haloalkoxy; -   R^(b), R^(c) are hydrogen, or one of the substituents mentioned     above under R^(a); and -   R^(d) is hydrogen or C₁-C₄-alkyl;     where the 5-membered heterocycle is attached to the isoxazoline     skeleton in the position ortho to the heteroatom.

Particular preference is also given to the 3-heteroaryl-substituted isoxazolines of the formula I in which

-   X is X⁶, where -   R^(a) is halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino,     C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,     C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl; -   R^(b) is hydrogen, or one of the substituents mentioned above under     R^(a);     preferably -   X is X⁶, where -   R^(a) is halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino,     C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,     C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl; -   R^(b) is hydrogen, or one of the substituents mentioned above under     R^(a);     where the 5-membered heterocycle is attached to the isoxazoline     skeleton in the position ortho to a heteroatom;     with particular preference -   X is X⁶, where -   R^(a) is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or     C₁-C₆-haloalkoxy; -   R^(b) is hydrogen, or one of the substituents mentioned above under     R^(a);     where the 5-membered heterocycle is attached to the isoxazoline     skeleton in the position ortho to a heteroatom.

Preference is also given to the 3-heteroaryl-substituted isoxazolines of the formula I in which

-   R¹-R⁷ are hydrogen, C₁-C₄-alkyl, such as, for example, methyl or     ethyl, or C₁-C₄-haloalkyl, such as, for example, difluoromethyl,     trifluoromethyl or trichloromethyl;     -   particularly preferably hydrogen, methyl or trifluoromethyl;     -   very preferably hydrogen;     -   with particular preference, R¹, R², R⁴-R⁷ are hydrogen, methyl         or trifluoromethyl and R³ is hydrogen, methyl, ethyl or         trifluoromethyl;     -   with very particular preference, R¹, R², R⁴-R⁷ are hydrogen and         R³ is methyl.

Preference is also given to the 3-heteroaryl-substituted isoxazolines of the formula I in which

-   Y is aryl which may be partially or fully halogenated and/or may     carry one to three substituents from the group consisting of cyano,     nitro, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl,     C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkoxy,     C₁-C₆-alkylsulfonyl, phenyl, phenoxy and phenylcarbonyl; or     -   benzo[1,4]dioxanyl, benzo[1,3]dioxolanyl,         2,3-dihydrobenzofuranyl or benzimidazolyl; or     -   5- or 6-membered heteroaryl containing one to four nitrogen,         oxygen and/or sulfur atoms which may be partially or fully         halogenated and/or may carry one to three substituents from the         group consisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,         C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxycarbonyl;     -   particularly preferably aryl which may be partially halogenated         and/or may carry one or two substituents from the group         consisting of cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl and         C₁-C₆-alkylsulfonyl; or     -   benzo[1,4]dioxanyl, benzo[1,3]dioxolanyl,         2,3-dihydrobenzofuranyl or benzimidazolyl; or     -   5- or 6-membered heteroaryl containing one to four nitrogen,         oxygen and/or sulfur atoms which may be partially halogenated         and/or may carry one or two substituents from the group         consisting of C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkyl and         C₁-C₆-alkoxycarbonyl;     -   especially preferably aryl which may be partially halogenated         and/or may carry one or two substituents from the group         consisting of cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl and         C₁-C₄-alkylsulfonyl; or benzo[1,4]dioxanyl,         benzo[1,3]dioxolanyl, 2,3-dihydrobenzofuranyl or benzimidazolyl;         or     -   5- or 6-membered heteroaryl from the group consisting of         pyrazolyl, thiazolyl, isoxazolyl, thiadiazolyl and pyridyl which         may be partially halogenated and/or may carry one or two         substituents from the group consisting of C₁-C₆-alkyl,         C₁-C₆-alkoxy-C₁-C₄-alkyl and C₁-C₆-alkoxycarbonyl.

Preference is also given to the 3-heteroaryl-substituted isoxazolines of the formula I in which

-   Y is aryl which may be partially or fully halogenated and/or may     carry one to three substituents from the group consisting of cyano,     nitro, C₁-C₆-alkyl or C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl,     C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl-C₁-C₄-alkoxy,     C₁-C₆-alkylsulfonyl, phenyl, phenoxy and phenylcarbonyl; preferably     cyano, nitro, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,     C₁-C₆-haloalkyl or C₁-C₆-alkoxy;     -   particularly preferably aryl which may be partially halogenated         and/or may carry one or two substituents from the group         consisting of cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl and         C₁-C₆-alkylsulfonyl; preferably cyano, C₁-C₆-alkyl or         C₁-C₆-haloalkyl;     -   with particular preference aryl which may be partially         halogenated and/or may carry one or two substituents from the         group consisting of cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl and         C₁-C₄-alkylsulfonyl; preferably cyano.

Preference is also given to 3-heteroaryl-substituted isoxazolines of the formula I in which

-   Y is aryl which may be partially or fully halogenated and/or may     carry one or two substituents from the group consisting of cyano,     C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-alkylsulfonyl;     preferably cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;     -   particularly preferably aryl which is halogenated in one or both         of the positions ortho to the point of attachment and/or may         carry a substituent from the group consisting of cyano,         C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and         C₁-C₄-alkoxysulfonyl;     -   preferably cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;     -   with particular special preference aryl which is halogenated in         one or both positions ortho to the point of attachment.

Preference is also given to the 3-heteroaryl-substituted isoxazolines of the formula I in which

-   Y is phenyl which may be partially or fully halogenated and/or may     carry one to three substituents from the group consisting of cyano,     nitro, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl,     C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,     C₁-C₆-haloalkylthio, C₁-C₆-alkoxycarbonyl,     C₁-C₆-alkoxycarbonyl-C₁-C₄-alkoxy, C₁-C₆-alkylsulfonyl, phenyl,     phenoxy and phenylcarbonyl; preferably cyano, nitro, C₁-C₆-alkyl,     C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,     C₁-C₆-haloalkoxy, C₁-C₆-alkylthio and C₁-C₆-haloalkylthio;     -   particularly preferably phenyl which may be partially or fully         halogenated and/or may carry one to three substituents from the         group consisting of cyano, nitro, C₁-C₆-alkyl, C₂-C₆-alkenyl,         C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,         C₁-C₆-alkoxycarbonyl; preferably cyano, nitro, C₁-C₆-alkyl,         C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl and C₁-C₆-alkoxy;     -   with particular special preference phenyl which may be partially         halogenated and/or may carry one or two substituents from the         group consisting of cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl and         C₁-C₆-alkylsulfonyl; preferably cyano, C₁-C₆-alkyl and         C₁-C₆-haloalkyl.

Preference is also given to the 3-heteroaryl-substituted isoxazolines of the formula I in which

-   Y is phenyl which may be partially or fully halogenated and/or may     carry one or two substituents from the group consisting of cyano,     C₁-C₄-alkyl and C₁-C₄-haloalkyl; particularly preferably phenyl     which is halogenated in the 2- and/or 6-position to the point of     attachment and/or may carry one substituent from the group     consisting of cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;     -   with particular special preference phenyl which is halogenated         in the 2- and/or 6-position to the point of attachment.

Preference is also given to the 3-heteroaryl-substituted isoxazolines of the formula I in which

-   Y is naphthyl which may be partially or fully halogenated and/or may     carry one to three substituents from the group consisting of cyano,     nitro, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl,     C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio and     C₁-C₆-haloalkylthio; particularly preferably naphthyl which may be     partially or fully halogenated and/or may carry one to three     substituents from the group consisting of cyano, nitro, C₁-C₆-alkyl,     C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl and C₁-C₆-alkoxy;     -   with particular special preference naphthyl which may be         partially halogenated and/or may carry one or two substituents         from the group consisting of cyano, C₁-C₆-alkyl and         C₁-C₆-haloalkyl.

Preference is also given to the 3-heteroaryl-substituted isoxazolines of the formula I in which

-   Y is naphthyl which may be partially or fully halogenated and/or may     carry one or two substituents from the group consisting of cyano,     C₁-C₄-alkyl and C₁-C₄-haloalkyl; particularly preferably naphthyl     which is halogenated in one or both of the positions ortho to the     point of attachment and/or may carry one substituent from the group     consisting of cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl;     -   with particular special preference naphthyl which is halogenated         in one or both of the positions ortho to the point of         attachment.

Preference is also given to the 3-heteroaryl-substituted isoxazolines of the formula I in which

-   Y is 5-membered heteroaryl having one to four nitrogen atoms or     having one to 3 nitrogen atoms and one oxygen or sulfur atom or one     oxygen or sulfur atom; or 6-membered heteroaryl having one to 4     nitrogen atoms; where the heterocycles may be partially or fully     halogenated and/or may carry one to three substituents from the     group consisting of cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,     C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxycarbonyl and     C₁-C₆-alkylsulfonyl;     -   particularly preferably 5-membered heteroaryl having one to four         nitrogen atoms or having one to 3 nitrogen atoms and one oxygen         or sulfur atom or one oxygen or sulfur atom; or     -   6-membered heteroaryl having one to 4 nitrogen atoms;     -   where the heterocycles may be partially or fully halogenated         and/or may carry one to three substituents from the group         consisting of cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy-C₁-C₄-alkyl and C₁-C₆-alkoxycarbonyl;     -   with particular special preference 5- or 6-membered heteroaryl         from the group consisting of pyrazolyl, thiazolyl, isoxazolyl,         thiadiazolyl and pyridyl, where the 5- or 6-membered heteroaryl         may be partially halogenated and/or may carry one or two         substituents from the group consisting of cyano, C₁-C₄-alkyl,         C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl and         C₁-C₄-alkoxycarbonyl.

Preference is also given to the 3-heteroaryl-substituted isoxazolines of the formula I in which

-   X is 6-membered heteroaryl having one to three nitrogen atoms,     -   preferably 6-membered heteroaryl having one or two nitrogen         atoms,     -   in particular pyridyl, pyrimidyl and pyrazinyl, very preferably         pyridyl and pyrimidyl;     -   where the 6-membered heteroaryl is substituted as described         above; -   R¹-R⁷ are hydrogen, C₁-C₄-alkyl, such as, for example, methyl or     ethyl, or C₁-C₄-haloalkyl, such as, for example, difluoromethyl,     trifluoromethyl or trichloromethyl;     -   particularly preferably hydrogen, methyl or trifluoromethyl;     -   very preferably hydrogen;     -   with particular preference, R¹, R², R⁴-R⁷ are hydrogen, methyl         or trifluoromethyl and R³ is hydrogen, methyl, ethyl or         trifluoromethyl; with very particular preference, R¹, R², R⁴-R⁷         are hydrogen and R³ is methyl; and -   Y is aryl which may be partially or fully halogenated and/or may     carry one or two substituents from the group consisting of cyano,     C₁-C₄-alkyl and C₁-C₄-haloalkyl;     -   particularly preferably aryl which is halogenated in one or both         of the positions ortho to the point of attachment and/or may         carry one substituent from the group consisting of cyano,         C₁-C₄-alkyl and C₁-C₄-haloalkyl;     -   with particular special preference aryl which is halogenated in         one or both of the positions ortho to the point of attachment.

Preference is also given to the 3-heteroaryl-substituted isoxazolines of the formula I in which

-   X is X¹, where -   R^(a) is halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino,     C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,     C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl; -   R^(b) is hydrogen, or one of the substituents mentioned under R^(a);     and -   R^(d) is hydrogen or C₁-C₆-alkyl,     -   preferably hydrogen or C₁-C₄-alkyl;         with particular preference -   X is X¹, where -   R^(a) is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or     C₁-C₆-haloalkoxy; -   R^(b) is hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,     C₁-C₆-alkoxy or C₁-C₆-haloalkoxy; and -   R^(d) is hydrogen or C₁-C₄-alkyl; -   R¹-R⁷ are hydrogen, C₁-C₄-alkyl, such as, for example, methyl or     ethyl, or C₁-C₄-haloalkyl, such as, for example, difluoromethyl,     trifluoromethyl or trichloromethyl; particularly preferably     hydrogen, methyl or trifluoromethyl;     -   very preferably hydrogen;     -   with particular preference, R¹, R², R⁴-R⁷ are hydrogen, methyl         or trifluoromethyl and R³ is hydrogen, methyl, ethyl or         trifluoromethyl; with very particular preference, R¹, R², R⁴-R⁷         are hydrogen and R³ is methyl; and -   Y is aryl which may be partially or fully halogenated and/or may     carry one or two substituents from the group consisting of cyano,     C₁-C₄-alkyl and C₁-C₄-haloalkyl; particlarly preferably aryl which     is halogenated in one or both of the positions ortho to the point of     attachment and/or may carry one substituent from the group     consisting of cyano, C₁-C₄-alkyl and C₁-C₄-haloalkyl; with     particular special preference aryl which is halogenated in one or     both of the positions ortho to the point of attachment.

Particular preference is also given to the 3-heteroaryl-substituted isoxazolines of the formula I in which

-   X is X⁵, where -   R^(a) is halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino,     C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,     C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl; -   R^(b), R^(c) are hydrogen, or one of the substituents mentioned     above under R^(a); and -   R^(d) is hydrogen or C₁-C₆-alkyl,     -   preferably hydrogen or C₁-C₄-alkyl;         preferably -   X is X⁵, where -   R^(a) is halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino,     C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,     C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl; -   R^(b), R^(c) are hydrogen, or one of the substituents mentioned     above under R^(a); and -   R^(d) is hydrogen or C₁-C₄-alkyl;     where the 5-membered heterocycle is attached to the isoxazoline     skeleton in the position ortho to the heteroatom;     with particular preference -   X is X⁵, where -   R^(a) is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or     C₁-C₆-haloalkoxy; -   R^(b), R^(c) are hydrogen, or one of the substituents mentioned     above under R^(a); and -   R^(d) is hydrogen or C₁-C₄-alkyl;     where the 5-membered heterocycle is attached to the isoxazoline     skeleton in the position ortho to the heteroatom, -   R¹-R⁷ are hydrogen, C₁-C₄-alkyl, such as, for example, methyl or     ethyl, or C₁-C₄-haloalkyl, such as, for example, difluoromethyl,     trifluoromethyl or trichloromethyl;     -   particularly preferably hydrogen, methyl or trifluoromethyl;     -   very preferably hydrogen;     -   with particular preference, R¹, R², R⁴-R⁷ are hydrogen, methyl         or trifluoromethyl and R³ is hydrogen, methyl, ethyl or         trifluoromethyl; with very particular preference, R¹, R², R⁴-R⁷         are hydrogen and R³ is methyl; and -   Y is aryl which may be partially or fully halogenated and/or may     carry one or two substituents from the group consisting of cyano,     C₁-C₄-alkyl and C₁-C₄-haloalkyl;     -   particularly preferably aryl which is halogenated in one or both         of the positions ortho to the point of attachment and/or may         carry one substituent from the group consisting of cyano,         C₁-C₄-alkyl and C₁-C₄-haloalkyl;     -   with particular special preference aryl which is halogenated in         one or both of the positions ortho to the point of attachment.

Particular preference is also given to the 3-heteroaryl-substituted isoxazolines of the formula I in which

-   X is X⁶, where -   R^(a) is halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino,     C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,     C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl, -   R^(b) is hydrogen, or one of the substituents mentioned above under     R^(a);     preferably -   X is X⁶, where -   R^(a) is halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino,     C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,     C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl; -   R^(b) is hydrogen, or one of the substituents mentioned above under     R^(a);     where the 5-membered heterocycle is attached to the isoxazoline     skeleton in the position ortho to a heteroatom;     with particular preference -   X is X⁶, where -   R^(a) is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or     C₁-C₆-haloalkoxy, -   R^(b) is hydrogen, or one of the substituents mentioned above under     R^(a);     where the 5-membered heterocycle is attached to the isoxazoline     skeleton in a position ortho to a heteroatom; -   R¹-R⁷ are hydrogen, C₁-C₄-alkyl, such as, for example, methyl or     ethyl, or C₁-C₄-haloalkyl, such as, for example, difluoromethyl,     trifluoromethyl or trichloromethyl;     -   particularly preferably hydrogen, methyl or trifluoromethyl;     -   very preferably hydrogen;     -   with particular preference, R¹, R², R⁴-R⁷ are hydrogen, methyl         or trifluoromethyl and R³ is hydrogen, methyl, ethyl or         trifluoromethyl; with very particular preference, R¹, R², R⁴-R⁷         are hydrogen and R³ is methyl, and -   Y is aryl which may be partially or fully halogenated and/or may     carry one or two substituents from the group consisting of cyano,     C₁-C₄-alkyl and C₁-C₄-haloalkyl;     -   particularly preferably aryl which is halogenated in one or both         of the positions ortho to the point of attachment and/or may         carry one substituent from the group consisting of cyano,         C₁-C₄-alkyl and C₁-C₄-haloalkyl;     -   with particular special preference aryl which is halogenated in         one or both of the positions ortho to the point of attachment.

Most preferred are the compounds of the formula I.a (corresponds to the formula I where R¹, R², R⁴-R⁷=hydrogen, R³=methyl), in particular the compounds of the formulae I.a.1 to I.a.234 of Table 1, where the definitions of the variables R¹ to R⁷, X and Y are of particular importance for the compounds according to the invention not only in combination with one another but in each case also on their own.

TABLE 1 I.a

No. X R′ R″ I.a.1 4-fluoropyrid-3-yl H H I.a.2 4-fluoropyrid-3-yl F H I.a.3 4-fluoropyrid-3-yl F F I.a.4 3-chloropyrid-2-yl H H I.a.5 3-chloropyrid-2-yl F H I.a.6 3-chloropyrid-2-yl F F I.a.7 4-chloropyrid-3-yl H H I.a.8 4-chloropyrid-3-yl F H I.a.9 4-chloropyrid-3-yl F F I.a.10 4-bromopyrid-3-yl H H I.a.11 4-bromopyrid-3-yl F H I.a.12 4-bromopyrid-3-yl F F I.a.13 2-methylpyrid-3-yl H H I.a.14 2-methylpyrid-3-yl F H I.a.15 2-methylpyrid-3-yl F F I.a.16 4-methylpyrid-3-yl H H I.a.17 4-methylpyrid-3-yl F H I.a.18 4-methylpyrid-3-yl F F I.a.19 2-trifluoromethylpyrid-3-yl H H I.a.20 2-trifluoromethylpyrid-3-yl F H I.a.21 2-trifluoromethylpyrid-3-yl F F I.a.22 2-methoxypyrid-3-yl H H I.a.23 2-methoxypyrid-3-yl F H I.a.24 2-methoxypyrid-3-yl F F I.a.25 2,6-difluoropyrid-3-yl H H I.a.26 2,6-difluoropyrid-3-yl F H I.a.27 2,6-difluoropyrid-3-yl F F I.a.28 2,3-dichloropyrid-4-yl H H I.a.29 2,3-dichloropyrid-4-yl F H I.a.30 2,3-dichloropyrid-4-yl F F I.a.31 2,4-dichloropyrid-3-yl H H I.a.32 2,4-dichloropyrid-3-yl F H I.a.33 2,4-dichloropyrid-3-yl F F I.a.34 2,6-dichloropyrid-3-yl H H I.a.35 2,6-dichloropyrid-3-yl F H I.a.36 2,6-dichloropyrid-3-yl F F I.a.37 2,6-dibromopyrid-3-yl H H I.a.38 2,6-dibromopyrid-3-yl F H I.a.39 2,6-dibromopyrid-3-yl F F I.a.40 2,4-dimethylpyrid-3-yl H H I.a.41 2,4-dimethylpyrid-3-yl F H I.a.42 2,4-dimethylpyrid-3-yl F F I.a.43 2,6-dimethylpyrid-3-yl H H I.a.44 2,6-dimethylpyrid-3-yl F H I.a.45 2,6-dimethylpyrid-3-yl F F I.a.46 2-Fluoro-6-methylpyrid-3-yl H H I.a.47 2-Fluoro-6-methylpyrid-3-yl F H I.a.48 2-Fluoro-6-methylpyrid-3-yl F F I.a.49 2-chloro-6-methylpyrid-3-yl H H I.a.50 2-chloro-6-methylpyrid-3-yl F H I.a.51 2-chloro-6-methylpyrid-3-yl F F I.a.52 3-chloro-6-methylpyrid-2-yl H H I.a.53 3-chloro-6-methylpyrid-2-yl F H I.a.54 3-chloro-6-methylpyrid-2-yl F F I.a.55 3-chloro-5-methylpyrid-4-yl H H I.a.56 3-chloro-5-methylpyrid-4-yl F H I.a.57 3-chloro-5-methylpyrid-4-yl F F I.a.58 2-bromo-6-methylpyrid-3-yl H H I.a.59 2-bromo-6-methylpyrid-3-yl F H I.a.60 2-bromo-6-methylpyrid-3-yl F F I.a.61 2-methyl-3-chloropyrid-4-yl H H I.a.62 2-methyl-3-chloropyrid-4-yl F H I.a.63 2-methyl-3-chloropyrid-4-yl F F I.a.64 2-methyl-6-chloropyrid-3-yl H H I.a.65 2-methyl-6-chloropyrid-3-yl F H I.a.66 2-methyl-6-chloropyrid-3-yl F F I.a.67 2,4,6-trichloropyrid-3-yl H H I.a.68 2,4,6-trichloropyrid-3-yl F H I.a.69 2,4,6-trichloropyrid-3-yl F F I.a.70 2,4,6-trimethylpyrid-3-yl H H I.a.71 2,4,6-trimethylpyrid-3-yl F H I.a.72 2,4,6-trimethylpyrid-3-yl F F I.a.73 2-fluoro-4,6-dimethylpyrid-3-yl H H I.a.74 2-fluoro-4,6-dimethylpyrid-3-yl F H I.a.75 2-fluoro-4,6-dimethylpyrid-3-yl F F I.a.76 2-chloro-4,6-dimethylpyrid-3-yl H H I.a.77 2-chloro-4,6-dimethylpyrid-3-yl F H I.a.78 2-chloro-4,6-dimethylpyrid-3-yl F F I.a.79 5-chloro-2,3-dimethylpyrid-4-yl H H I.a.80 5-chloro-2,3-dimethylpyrid-4-yl F H I.a.81 5-chloro-2,3-dimethylpyrid-4-yl F F I.a.82 3,5-dichloro-2-methylpyrid-4-yl H H I.a.83 3,5-dichloro-2-methylpyrid-4-yl F H I.a.84 3,5-dichloro-2-methylpyrid-4-yl F F I.a.85 2-bromo-4,6-dimethylpyrid-3-yl H H I.a.86 2-bromo-4,6-dimethylpyrid-3-yl F H I.a.87 2-bromo-4,6-dimethylpyrid-3-yl F F I.a.88 4-chloropyrimidin-5-yl H H I.a.89 4-chloropyrimidin-5-yl F H I.a.90 4-chloropyrimidin-5-yl F F I.a.91 4,6-dichloropyrimidin-5-yl H H I.a.92 4,6-dichloropyrimidin-5-yl F H I.a.93 4,6-dichloropyrimidin-5-yl F F I.a.94 4-methylpyrimidin-5-yl H H I.a.95 4-methylpyrimidin-5-yl F H I.a.96 4-methylpyrimidin-5-yl F F I.a.97 4,6-dimethylpyrimidin-5-yl H H I.a.98 4,6-dimethylpyrimidin-5-yl F H I.a.99 4,6-dimethylpyrimidin-5-yl F F I.a.100 2-chloropyrazin-3-yl H H I.a.101 2-chloropyrazin-3-yl F H I.a.102 2-chloropyrazin-3-yl F F I.a.103 2-methylpyrazin-3-yl H H I.a.104 2-methylpyrazin-3-yl F H I.a.105 2-methylpyrazin-3-yl F F I.a.106 3-chloropyridazin-4-yl H H I.a.107 3-chloropyridazin-4-yl F H I.a.108 3-chloropyridazin-4-yl F F I.a.109 3-methylpyridazin-4-yl H H I.a.110 3-methylpyridazin-4-yl F H I.a.111 3-methylpyridazin-4-yl F F I.a.112 2-chlorofuryl-3-yl H H I.a.113 2-chlorofuryl-3-yl F H I.a.114 2-chlorofuryl-3-yl F F I.a.115 2-methylfuryl-3-yl H H I.a.116 2-methylfuryl-3-yl F H I.a.117 2-methylfuryl-3-yl F F I.a.118 2,5-dichlorofuryl-3-yl H H I.a.119 2,5-dichlorofuryl-3-yl F H I.a.120 2,5-dichlorofuryl-3-yl F F I.a.121 2-chloro-4-methylfuryl-3-yl H H I.a.122 2-chloro-4-methylfuryl-3-yl F H I.a.123 2-chloro-4-methylfuryl-3-yl F F I.a.124 2-chloro-4,5-dimethylfuryl-3-yl H H I.a.125 2-chloro-4,5-dimethylfuryl-3-yl F H I.a.126 2-chloro-4,5-dimethylfuryl-3-yl F F I.a.127 1,5-dimethylimidazol-4-yl H H I.a.128 1,5-dimethylimidazol-4-yl F H I.a.129 1,5-dimethylimidazol-4-yl F F I.a.130 1-methyl-5-chloroimidazol-4-yl H H I.a.131 1-methyl-5-chloroimidazol-4-yl F H I.a.132 1-methyl-5-chloroimidazol-4-yl F F I.a.133 1,2,5-trimethylimidazol-4-yl H H I.a.134 1,2,5-trimethylimidazol-4-yl F H I.a.135 1,2,5-trimethylixnidazol-4-yl F F I.a.136 1-methyl-2,5-dichloroimidazol-4-yl H H I.a.137 1-methyl-2,5-dichloroimidazol-4-yl F H I.a.138 1-methyl-2,5-dichloroimidazol-4-yl F F I.a.139 5-chlorooxazol-4-yl H H I.a.140 5-chlorooxazol-4-yl F H I.a.141 5-chlorooxazol-4-yl F F I.a.142 5-methyloxazol-4-yl H H I.a.143 5-methyloxazol-4-yl F H I.a.144 5-methyloxazol-4-yl F F I.a.145 5-chloroisoxazol-4-yl H H I.a.146 5-chloroisoxazol-4-yl F H I.a.147 5-chloroisoxazol-4-yl F F I.a.148 5-methylisoxazol-4-yl H H I.a.149 5-methylisoxazol-4-yl F H I.a.150 5-methylisoxazol-4-yl F F I.a.151 5-chlorothiazol-4-yl H H I.a.152 5-chlorothiazol-4-yl F H I.a.153 5-chlorothiazol-4-yl F F I.a.154 5-methylthiazol-4-yl H H I.a.155 5-methylthiazol-4-yl F H I.a.156 5-methylthiazol-4-yl F F I.a.157 5-chloroisothiazol-4-yl H H I.a.158 5-chloroisothiazol-4-yl F H I.a.159 5-chloroisothiazol-4-yl F F I.a.160 5-methylisothiazol-4-yl H H I.a.161 5-methylisothiazol-4-yl F H I.a.162 5-methylisothiazol-4-yl F F I.a.163 1,5-dimethyl-1,2,3-triazol-4-yl H H I.a.164 1,5-dimethyl-1,2,3-triazol-4-yl F H I.a.165 1,5-dimethyl-1,2,3-triazol-4-yl F F I.a.166 1-methyl-4-chloro-1,2,3-triazol-5-yl H H I.a.167 1-methyl-4-chloro-1,2,3-triazol-5-yl F H I.a.168 1-methyl-4-chloro-1,2,3-triazol-5-yl F F I.a.169 1-methyl-5-chloro-1,2,3-triazol-4-yl H H I.a.170 1-methyl-5-chloro-1,2,3-triazol-4-yl F H I.a.171 1-methyl-5-chloro-1,2,3-triazol-4-yl F F I.a.172 3-chloro-1,2,5-oxadiazol-4-yl H H I.a.173 3-chloro-1,2,5-oxadiazol-4-yl F H I.a.174 3-chloro-1,2,5-oxadiazol-4-yl F F I.a.175 3-methyl-1,2,5-oxadiazol-4-yl H H I.a.176 3-methyl-1,2,5-oxadiazol-4-yl F H I.a.177 3-methyl-1,2,5-oxadiazol-4-yl F F I.a.178 3-chloro-1,2,4-oxadiazol-5-yl H H I.a.179 3-chloro-1,2,4-oxadiazol-5-yl F H I.a.180 3-chloro-1,2,4-oxadiazol-5-yl F F I.a.181 5-chloro-1,2,4-oxadiazol-3-yl H H I.a.182 5-chloro-1,2,4-oxadiazol-3-yl F H I.a.183 5-chloro-1,2,4-oxadiazol-3-yl F F I.a.184 3-methyl-1,2,4-oxadiazol-5-yl H H I.a.185 3-methyl-1,2,4-oxadiazol-5-yl F H I.a.186 3-methyl-1,2,4-oxadiazol-5-yl F F I.a.187 5-methyl-1,2,4-oxadiazol-3-yl H H I.a.188 5-methyl-1,2,4-oxadiazol-3-yl F H I.a.189 5-methyl-1,2,4-oxadiazol-3-yl F F I.a.190 5-chloro-1,3,4-oxadiazol-2-yl H H I.a.191 5-chloro-1,3,4-oxadiazol-2-yl F H I.a.192 5-chloro-1,3,4-oxadiazol-2-yl F F I.a.193 5-chloro-1,2,3-thiadiazol-4-yl H H I.a.194 5-chloro-1,2,3-thiadiazol-4-yl F H I.a.195 5-chloro-1,2,3-thiadiazol-4-yl F F I.a.196 5-methyl-1,2,3-thiadiazol-4-yl H H I.a.197 5-methyl-1,2,3-thiadiazol-4-yl F H I.a.198 5-methyl-1,2,3-thiadiazol-4-yl F F I.a.199 4-cyanopyrid-3-yl F F I.a.200 4-cyanopyrid-3-yl H H I.a.201 4-cyanopyrid-3-yl F F I.a.202 4-trifluoromethylpyrid-3-yl F F I.a.203 4-trifluoromethylpyrid-3-yl H H I.a.204 4-trifluoromethylpyrid-3-yl F H I.a.205 4-methoxypyrid-3-yl F F I.a.206 4-methoxypyrid-3-yl H H I.a.207 4-methoxypyrid-3-yl F H I.a.208 2-fluoropyrid-3-yl F F I.a.209 2-fluoropyrid-3-yl H H I.a.210 2-fluoropyrid-3-yl F H I.a.211 2-chloropyrid-3-yl F F I.a.212 2-chloropyrid-3-yl H H I.a.213 2-chloropyrid-3-yl F H I.a.214 2-bromopyrid-3-yl F F I.a.215 2-bromopyrid-3-yl H H I.a.216 2-bromopyrid-3-yl F H I.a.217 2-cyanopyrid-3-yl F F I.a.218 2-cyanopyrid-3-yl H H I.a.219 2-cyanopyrid-3-yl F H I.a.220 2-fluoropyrazin-3-yl F F I.a.221 2-fluoropyrazin-3-yl H H I.a.222 2-fluoropyrazin-3-yl F H I.a.223 2-bromopyrazin-3-yl F F I.a.224 2-bromopyrazin-3-yl H H I.a.225 2-bromopyrazin-3-yl F H I.a.226 2-cyanopyrazin-3-yl F F I.a.227 2-cyanopyrazin-3-yl H H I.a.228 2-cyanopyrazin-3-yl F H I.a.229 2-trifluoromethylpyrazin-3-yl F F I.a.230 2-trifluoromethylpyrazin-3-yl H H I.a.231 2-trifluoromethylpyrazin-3-yl F H I.a.232 2-methoxypyrazin-3-yl F F I.a.233 2-methoxypyrazin-3-yl H H I.a.234 2-methoxypyrazin-3-yl F H

Likewise most preferred are the compounds of the formula I.b, in particular the compounds of the formulae I.b.1 to I.b.234 which differ from the corresponding compounds of the formulae I.a.1 to I.a.234 in that R³ is hydrogen.

Likewise most preferred are the compounds of the formula I.c, in particular the compounds of the formulae I.c.1 to I.c.234 which differ from the corresponding compounds of the formulae I.a.1 to I.a.234 in that R³ is ethyl.

Likewise most preferred are the compounds of the formula I.d, in particular the compounds of the formulae I.d.1 to I.d.234 which differ from the corresponding compounds of the formulae I.a.1 to I.a.234 in that Y is correspondingly substituted naphth-2-yl.

Likewise most preferred are the compounds of the formula I.e, in particular the compounds of the formulae I.e.1 to I.e.234 which differ from the corresponding compounds of the formulae I.a.1 to I.a.234 in that R³ is hydrogen and Y is correspondingly substituted naphth-2-yl.

Likewise most preferred are the compounds of the formula I.f (corresponding to formula I where X=4-fluoropyrid-3-yl and R¹, R², R⁴-R⁷=hydrogen), in particular the compounds of the formulae I.f.1 to I.f.228 of table 1A, where the definitions of the variables R¹ to R⁷, X and Y are of particular importance for the compounds according to the invention not only in combination with one another but in each case also on their own.

TABLE 1A I.f

No. R³ Y I.f.1 H 3-fluorophenyl I.f.2 CH₃ 3-fluorophenyl I.f.3 C₂H₅ 3-fluorophenyl I.f.4 H 4-fluorophenyl I.f.5 CH₃ 4-fluorophenyl I.f.6 C₂H₅ 4-fluorophenyl I.f.7 H 2-chlorophenyl I.f.8 CH₃ 2-chlorophenyl I.f.9 C₂H₅ 2-chlorophenyl I.f.10 H 3-chlorophenyl I.f.11 CH₃ 3-chlorophenyl I.f.12 C₂H₅ 3-chlorophenyl I.f.13 H 4-chlorophenyl I.f.14 CH₃ 4-chlorophenyl I.f.15 C₂H₅ 4-chlorophenyl I.f.16 H 2-bromophenyl I.f.17 CH₃ 2-bromophenyl I.f.18 C₂H₅ 2-bromophenyl I.f.19 H 3-bromophenyl I.f.20 CH₃ 3-bromophenyl I.f.21 C₂H₅ 3-bromophenyl I.f.22 H 4-bromophenyl I.f.23 CH₃ 4-bromophenyl I.f.24 C₂H₅ 4-bromophenyl I.f.25 H 2-iodophenyl I.f.26 CH₃ 2-iodophenyl I.f.27 C₂H₅ 2-iodophenyl I.f.28 H 2,4-difluorophenyl I.f.29 CH₃ 2,4-difluoropheny) I.f.30 C₂H₅ 2,4-difluorophenyl I.f.31 H 3,5-difluorophenyl I.f.32 CH₃ 3,5-difluorophenyl I.f.33 C₂H₅ 3,5-difluorophenyl I.f.34 H 2,6-dichlorophenyl I.f.35 CH₃ 2,6-dichlorophenyl I.f.36 C₂H₅ 2,6-dichlorophenyl I.f.37 H 2,4-dichlorophenyl I.f.38 CH₃ 2,4-dichlorophenyl I.f.39 C₂H₅ 2,4-dichlorophenyl I.f.40 H 3,4-dichlorophenyl I.f.41 CH₃ 3,4-dichlorophenyl I.f.42 C₂H₅ 3,4-dichlorophenyl I.f.43 H 2,4,6-trichlorophenyl I.f.44 CH₃ 2,4,6-trichlorophenyl I.f.45 C₂H₅ 2,4,6-trichlorophenyl I.f.46 H 2,3,5-trichlorophenyl I.f.47 CH₃ 2,3,5-trichlorophenyl I.f.48 C₂H₅ 2,3,5-trichlorophenyl I.f.49 H 2,3,4,5,6-pentafluorophenyl I.f.50 CH₃ 2,3,4,5,6-pentafluorophenyl I.f.51 C₂H₅ 2,3,4,5,6-pentafluorophenyl I.f.52 H 2-nitrophenyl I.f.53 CH₃ 2-nitrophenyl I.f.54 C₂H₅ 2-nitrophenyl I.f.55 H 3-nitrophenyl I.f.56 CH₃ 3-nitrophenyl I.f.57 C₂H₅ 3-nitrophenyl I.f.58 H 4-nitrophenyl I.f.59 CH₃ 4-nitrophenyl I.f.60 C₂H₅ 4-nitrophenyl I.f.61 H 2-cyanophenyl I.f.62 CH₃ 2-cyanophenyl I.f.63 C₂H₅ 2-cyanophenyl I.f.64 H 3-cyanophenyl I.f.65 CH₃ 3-cyanophenyl I.f.66 C₂H₅ 3-cyanophenyl I.f.67 H 4-cyanophenyl I.f.68 CH₃ 4-cyanophenyl I.f.69 C₂H₅ 4-cyanophenyl I.f.70 H 2-methylphenyl I.f.71 CH₃ 2-methylphenyl I.f.72 C₂H₅ 2-methylphenyl I.f.73 H 3-methylphenyl I.f.74 CH₃ 3-methylphenyl I.f.75 C₂H₅ 3-methylphenyl I.f.76 H 4-methylphenyl I.f.77 CH₃ 4-methylphenyl I.f.78 C₂H₅ 4-methylphenyl I.f.79 H 4-ethylphenyl I.f.80 CH₃ 4-ethylphenyl I.f.81 C₂H₅ 4-ethylphenyl I.f.82 H 2,5-dimethylphenyl I.f.83 CH₃ 2,5-dimethylphenyl I.f.84 C₂H₅ 2,5-dimethylphenyl I.f.85 H 3,4-dimethylphenyl I.f.86 CH₃ 3,4-dimethylphenyl I.f.87 C₂H₅ 3,4-dimethylphenyl I.f.88 H 2,4-dimethylphenyl I.f.89 CH₃ 2,4-dimethylphenyl I.f.90 C₂H₅ 2,4-dimethylphenyl I.f.91 H 2,4,6-trimethylphenyl I.f.92 CH₃ 2,4,6-trimethylphenyl I.f.93 C₂H₅ 2,4,6-trimethylphenyl I.f.94 H 2-trifluoromethylphenyl I.f.95 CH₃ 2-trifluoromethylphenyl I.f.96 C₂H₅ 2-trifluoromethylphenyl I.f.97 H 3-trifluoromethylphenyl I.f.98 CH₃ 3-trifluoromethylphenyl I.f.99 C₂H₅ 3-trifluoromethylphenyl I.f.100 H 4-trifluoromethylphenyl I.f.101 CH₃ 4-trifluoromethylphenyl I.f.102 C₂H₅ 4-trifluoromethylphenyl I.f.103 H 2-methoxyphenyl I.f.104 CH₃ 2-methoxyphenyl I.f.105 C₂H₅ 2-methoxyphenyl I.f.106 H 3-methoxyphenyl I.f.107 CH₃ 3-methoxyphenyl I.f.108 C₂H₅ 3-methoxyphenyl I.f.109 H 4-methoxyphenyl I.f.110 CH₃ 4-methoxyphenyl I.f.111 C₂H₅ 4-methoxyphenyl I.f.112 H 3,4,5-trimethoxyphenyl I.f.113 CH₃ 3,4,5-trimethoxyphenyl I.f.114 C₂H₅ 3,4,5-trimethoxyphenyl I.f.115 H 3-trifluoromethoxyphenyl I.f.116 CH₃ 3-trifluoromethoxyphenyl I.f.117 C₂H₅ 3-trifluoromethoxyphenyl I.f.118 H 2-difluoromethoxyphenyl I.f.119 CH₃ 2-difluoromethoxyphenyl I.f.120 C₂H₅ 2-difluoromethoxyphenyl I.f.121 H 2-(ethoxycarbonylmethoxy)phenyl I.f.122 CH₃ 2-(ethoxycarbonylmethoxy)phenyl I.f.123 C₂H₅ 2-(ethoxycarbonylmethoxy)phenyl I.f.124 H 4-(phenyl)phenyl I.f.125 CH₃ 4-(phenyl)phenyl I.f.126 C₂H₅ 4-(phenyl)phenyl I.f.127 H 3-phenoxyphenyl I.f.128 CH₃ 3-phenoxyphenyl I.f.129 C₂H₅ 3-phenoxyphenyl I.f.130 H 2-methyl-3-(phenyl)phenyl I.f.131 CH₃ 2-methyl-3-(phenyl)phenyl I.f.132 C₂H₅ 2-methyl-3-(phenyl)phenyl I.f.133 H 3-phenoxyphenyl I.f.134 CH₃ 3-phenoxyphenyl I.f.135 C₂H₅ 3-phenoxyphenyl I.f.136 H 3-(phenylcarbonyl)phenyl I.f.137 CH₃ 3-(phenylcarbonyl)phenyl I.f.138 C₂H₅ 3-(phenylcarbonyl)phenyl I.f.139 H 4-(methoxycarbonyl)phenyl I.f.140 CH₃ 4-(methoxycarbonyl)phenyl I.f.141 C₂H₅ 4-(methoxycarbonyl)phenyl I.f.142 H 4-(isopropoxycarbonyl)phenyl I.f.143 CH₃ 4-(isopropoxycarbonyl)phenyl I.f.144 C₂H₅ 4-(isopropoxycarbonyl)phenyl I.f.145 H 2-chloro-6-nitrophenyl I.f.146 CH₃ 2-chloro-6-nitrophenyl I.f.147 C₂H₅ 2-chloro-6-nitrophenyl I.f.148 H 3-chloro-4-methoxyphenyl I.f.149 CH₃ 3-chloro-4-methoxyphenyl I.f.150 C₂H₅ 3-chloro-4-methoxyphenyl I.f.151 H 3-chloro-4-ethoxyphenyl I.f.152 CH₃ 3-chloro-4-ethoxyphenyl I.f.153 C₂H₅ 3-chloro-4-ethoxyphenyl I.f.154 H 2-ethyl-5-nitrophenyl I.f.155 CH₃ 2-ethyl-5-nitrophenyl I.f.156 C₂H₅ 2-ethyl-5-nitrophenyl I.f.157 H 2,3-dichloro-4-methoxyphenyl I.f.158 CH₃ 2,3-dichloro-4-methoxyphenyl I.f.159 C₂H₅ 2,3-dichloro-4-methoxyphenyl I.f.160 H 2,3-dichloro-4-isopropoxyphenyl I.f.161 CH₃ 2,3-dichloro-4-isopropoxyphenyl I.f.162 C₂H₅ 2,3-dichloro-4-isopropoxyphenyl I.f.163 H 2,4-dichloro-6-nitrophenyl I.f.164 CH₃ 2,4-dichloro-6-nitrophenyl I.f.165 C₂H₅ 2,4-dichloro-6-nitrophenyl I.f.166 H 2-chloro-3-methyl-4-(methyl-sulfonyl)phenyl I.f.167 CH₃ 2-chloro-3-methyl-4-(methyl-sulfonyl)phenyl I.f.168 C₂H₅ 2-chloro-3-methyl-4-(methyl-sulfonyl)phenyl I.f.169 H benzo[1,4]dioxan-6-yl I.f.170 CH₃ benzo[1,4]dioxan-6-yl I.f.171 C₂H₅ benzo[1,4]dioxan-6-yl I.f.172 H benzo[1,3]dioxolan-5-yl I.f.173 CH₃ benzo[1,3]dioxolan-5-yl I.f.174 C₂H₅ benzo[1,3]dioxolan-5-yl I.f.175 H 2,3-dihydrobenzofuran-2-yl I.f.176 CH₃ 2,3-dihydrobenzofuran-2-yl I.f.177 C₂H₅ 2,3-dihydrobenzofuran-2-yl I.f.178 H benzimidazol-2-yl I.f.179 CH₃ benzimidazol-2-yl I.f.180 C₂H₅ benzimidazol-2-yl I.f.181 H naphth-1-yl I.f.182 CH₃ naphth-1-yl I.f.183 C₂H₅ naphth-1-yl I.f.184 H 2-methylnaphth-1-yl I.f.185 CH₃ 2-methylnaphth-1-yl I.f.186 C₂H₅ 2-methylnaphth-1-yl I.f.187 H anthrancen-9-yl I.f.188 CH₃ anthrancen-9-yl I.f.189 C₂H₅ anthrancen-9-yl I.f.190 H 5-chloro-1-methylpyrazol-4-yl I.f.191 CH₃ 5-chloro-1-methylpyrazol-4-yl I.f.192 C₂H₅ 5-chloro-1-methylpyrazol-4-yl I.f.193 H 5-chloro-1-methyl-3-trifluoro-methylpyrazol-4-yl I.f.194 CH₃ 5-chloro-1-methyl-3-trifluoro-methylpyrazol-4-yl I.f.195 C₂H₅ 5-chloro-1-methyl-3-trifluoro-methylpyrazol-4-yl I.f.196 H thiazol-4-yl I.f.197 CH₃ thiazol-4-yl I.f.198 C₂H₅ thiazol-4-yl I.f.199 H 2-chlorothiazol-5-yl I.f.200 CH₃ 2-chlorothiazol-5-yl I.f.201 C₂H₅ 2-chlorothiazol-5-yl I.f.202 H 3-ethylisoxazol-5-yl I.f.203 CH₃ 3-ethylisoxazol-5-yl I.f.204 C₂H₅ 3-ethylisoxazol-5-yl I.f.205 H 3-n-propylisoxazol-5-yl I.f.206 CH₃ 3-n-propylisoxazol-5-yl I.f.207 C₂H₅ 3-n-propylisoxazol-5-yl I.f.208 H 3-(methoxymethyl)isoxazol-5-yl I.f.209 CH₃ 3-(methoxymethyl)isoxazol-5-yl I.f.210 C₂H₅ 3-(methoxymethyl)isoxazol-5-yl I.f.211 H 5-methoxymethyl-1,3,4-thiadiazol-2-yl I.f.212 CH₃ 5-methoxymethyl-1,3,4-thiadiazol-2-yl I.f.213 C₂H₅ 5-methoxymethyl-1,3,4-thiadiazol-2-yl I.f.214 H pyrid-2-yl I.f.215 CH₃ pyrid-2-yl I.f.216 C₂H₅ pyrid-2-yl I.f.217 H pyrid-3-yl I.f.218 CH₃ pyrid-3-yl I.f.219 C₂H₅ pyrid-3-yl I.f.220 H pyrid-4-yl I.f.221 CH₃ pyrid-4-yl I.f.222 C₂H₅ pyrid-4-yl I.f.223 H 2-chloropyrid-5-yl I.f.224 CH₃ 2-chloropyrid-5-yl I.f.225 C₂H₅ 2-chloropyrid-5-yl I.f.226 H 5-ethyl-3-(ethoxy-carbonyl)pyrid-2-yl I.f.227 CH₃ 5-ethyl-3-(ethoxy-carbonyl)pyrid-2-yl I.f.228 C₂H₅ 5-ethyl-3-(ethoxy-carbonyl)pyrid-2-yl

Likewise most preferred are the compounds of the formula I.g, in particular the compounds of the formulae I.g.1 to I.g.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 4-chloropyrid-3-yl.

Likewise most preferred are the compounds of the formula I.h, in particular the compounds of the formulae I.h.1 to I.h.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 4-bromopyrid-3-yl.

Likewise most preferred are the compounds of the formula I.i, in particular the compounds of the formulae I.i.1 to I.i.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 4-cyanopyrid-3-yl.

Likewise most preferred are the compounds of the formula I.k, in particular the compounds of the formulae I.k.1 to I.k.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 4-methylpyrid-3-yl.

Likewise most preferred are the compounds of the formula I.l, in particular the compounds of the formulae I.l.1 to I.l.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 4-trifluoromethylpyrid-3-yl.

Likewise most preferred are the compounds of the formula I.m, in particular the compounds of the formulae I.m.1 to I.m.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 4-methoxypyrid-3-yl.

Likewise most preferred are the compounds of the formula I.n, in particular the compounds of the formulae I.n.1 to I.n.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2-fluoropyrid-3-yl.

Likewise most preferred are the compounds of the formula I.o, in particular the compounds of the formulae I.o.1 to I.o.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2-chloropyrid-3-yl.

Likewise most preferred are the compounds of the formula I.p, in particular the compounds of the formulae I.p.1 to I.p.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2-bromopyrid-3-yl.

Likewise most preferred are the compounds of the formula I.q, in particular the compounds of the formulae I.q.1 to I.q.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2-cyanopyrid-3-yl.

Likewise most preferred are the compounds of the formula I.r, in particular the compounds of the formulae I.r.1 to I.r.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2-methylpyrid-3-yl.

Likewise most preferred are the compounds of the formula I.s, in particular the compounds of the formulae I.s.1 to I.s.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2-trifluoromethylpyrid-3-yl.

Likewise most preferred are the compounds of the formula I.t, in particular the compounds of the formulae I.t.1 to I.t.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2-methoxypyrid-3-yl.

Likewise most preferred are the compounds of the formula I.u, in particular the compounds of the formulae I.u.1 to I.u.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2,4-dichloropyrid-3-yl.

Likewise most preferred are the compounds of the formula I.v, in particular the compounds of the formulae I.v.1 to I.v.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2,4-dimethylpyrid-3-yl.

Likewise most preferred are the compounds of the formula I.w, in particular the compounds of the formulae I.w.1 to I.w.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2,6-difluoropyrid-3-yl.

Likewise most preferred are the compounds of the formula I.x, in particular the compounds of the formulae I.x.1 to I.x.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2,6-dichloropyrid-3-yl.

Likewise most preferred are the compounds of the formula I.y, in particular the compounds of the formulae I.y.1 to I.y.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2,6-dibromopyrid-3-yl.

Likewise most preferred are the compounds of the formula I.z, in particular the compounds of the formulae I.z.1 to I.z.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2,6-dimethylpyrid-3-yl.

Likewise most preferred are the compounds of the formula I.aa, in particular the compounds of the formulae I.aa.1 to I.aa.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2-chloro-6-methylpyrid-3-yl.

Likewise most preferred are the compounds of the formula I.ab, in particular the compounds of the formulae I.ab.1 to I.ab.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 6-chloro-2-methylpyrid-3-yl.

Likewise most preferred are the compounds of the formula I.ac, in particular the compounds of the formulae I.ac.1 to I.ac.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2,4,6-trichloropyrid-3-yl.

Likewise most preferred are the compounds of the formula I.ad, in particular the compounds of the formulae I.ad.1 to I.ad.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2,4-difluoro-6-methylpyrid-3-yl.

Likewise most preferred are the compounds of the formula I.ae, in particular the compounds of the formulae I.ae.1 to I.ae.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2,4,6-trimethylpyrid-3-yl.

Likewise most preferred are the compounds of the formula I.af, in particular the compounds of the formulae I.af.1 to I.af.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 4,6-dimethyl-2-fluoropyrid-3-yl.

Likewise most preferred are the compounds of the formula I.ag, in particular the compounds of the formulae I.ag.1 to I.ag.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2-chloro-4,6-dimethylpyrid-3-yl.

Likewise most preferred are the compounds of the formula I.ah, in particular the compounds of the formulae I.ah.1 to I.ah.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2-bromo-4-fluoro-6-methylpyrid-3-yl.

Likewise most preferred are the compounds of the formula I.ai, in particular the compounds of the formulae I.ai.1 to I.ai.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 3-chloropyrid-2-yl.

Likewise most preferred are the compounds of the formula I.ak, in particular the compounds of the formulae I.ak.1 to I.ak.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 3-chloro-6-methylpyrid-2-yl.

Likewise most preferred are the compounds of the formula I.al, in particular the compounds of the formulae I.al.1 to I.al.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 3,5-dichloropyrid-4-yl.

Likewise most preferred are the compounds of the formula I.am, in particular the compounds of the formulae I.am.1 to I.am.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2,3-dichloropyrid-4-yl.

Likewise most preferred are the compounds of the formula I.am, in particular the compounds of the formulae I.am.1 to I.am.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 3-chloro-2-methylpyrid-4-yl.

Likewise most preferred are the compounds of the formula I.ao, in particular the compounds of the formulae I.ao.1 to I.ao.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 3,5-dichloro-2-methylpyrid-4-yl.

Likewise most preferred are the compounds of the formula I.ap, in particular the compounds of the formulae I.ap.1 to I.ap.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 5-chloro-2,3-dimethylpyrid-4-yl.

Likewise most preferred are the compounds of the formula I.aq, in particular the compounds of the formulae I.aq.1 to I.aq.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2-fluoropyrazin-3-yl.

Likewise most preferred are the compounds of the formula I.ar, in particular the compounds of the formulae I.ar.1 to I.ar.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2-chloropyrazin-3-yl.

Likewise most preferred are the compounds of the formula I.as, in particular the compounds of the formulae I.as.1 to I.as.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2-bromopyrazin-3-yl.

Likewise most preferred are the compounds of the formula I.at, in particular the compounds of the formulae I.at.1 to I.at.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2-cyanopyrazin-3-yl.

Likewise most preferred are the compounds of the formula I.au, in particular the compounds of the formulae I.au.1 to I.au.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2-methylpyrazin-3-yl.

Likewise most preferred are the compounds of the formula I.av, in particular the compounds of the formulae I.av.1 to I.av.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2-trifluoromethylpyrazin-3-yl.

Likewise most preferred are the compounds of the formula I.aw, in particular the compounds of the formulae I.aw.1 to I.aw.228 which differ from the corresponding compounds of the formulae I.f.1 to I.f.228 in that X is 2-methoxypyrazin-3-yl.

The 3-heteroaryl-substituted isoxazolines of the formula I can be obtained by different routes, for example by the following process:

Process A

An aldoxime of the formula VII is, via the corresponding hydroxamic acid halide of the formula VI converted into a nitrile oxide of the formula V. The nitrile oxide of the formula V reacts with an allyl alcohol of the formula IV to give a 5-hydroxymethylisoxazoline of the formula III. This is then etherified with an arylmethyl derivative of the formula II to give the 3-heteroaryl-substituted isoxazoline of the formula I:

L¹ in formula II is a nucleophilically displaceable leaving group, such as halogen (e.g. chlorine, bromine or iodine), arylsulfonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, C₁-C₆-alkylsulfonyloxy or C₁-C₆-haloalkylsulfonyloxy, such as, for example, tolylsulfonyl or trifluoromethylsulfonyloxy, or another equivalent leaving group.

Hal in formula VI is halogen, preferably chlorine or bromine, with particular preference bromine.

The reaction of the 5-hydroxymethylisoxazoline of the formula III with an arylmethyl derivative of the formula II in the presence of a base to give the 3-heteroaryl-substituted isoxazoline of the formula I is usually carried out at temperatures of from 0° C. to 120° C., preferably from 10° C. to 80° C., in an inert organic solvent [cf. EP-0 334 120].

Suitable aprotic solvents are ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably diethyl ether, tert-butyl methyl ether, dioxane and tetrahydrofuran.

It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides, such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate and calcium carbonate, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines.

The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts, in excess or, if appropriate, as solvent.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to employ an excess of II, based on III.

Work-up and isolation of the products can be carried out in a manner known per se.

The arylmethyl derivatives of the formula II required for preparing the 3-heteroaryl-substituted isoxazolines of the formula I are known from the literature [cf. Organikum, 1979, pp. 213f., 413f.], or they can be prepared in accordance with the literature cited.

The nitrile oxides of the formula V required for preparing the 5-hydroxymethylisoxazolines of the formula III can be prepared in accordance with the literature in situ from the corresponding aldoximes of the formula VII via the stage of the hydroxamic acid halide of the formula VI [cf. Houben-Weyl, Methoden der organischen Chemie [Methods of organic chemistry], vol. E 5, 1985, p. 1591 ff. and literature cited therein], or they are known from the literature cited.

In general, the aldoxime of the formula VII is initially charged together with the allyl alcohol of the formula IV; using a halogenating agent, if appropriate with addition of base, the corresponding hydroxamic acid chloride of the formula VI is formed, and this is converted by further addition of base into the nitrile oxide of the formula V. The nitrile oxide of the formula V generated in this way then reacts with the allyl alcohol of the formula IV initially charged with the reaction mixture to give the 5-hydroxymethylisoxazoline of the formula III.

Furthermore, it is also possible to initially halogenate the aldoxime of the formula VIII to give the hydroxamic acid chloride of the formula VI, followed by addition of the allyl alcohol of the formula IV and the base. The nitrile oxide of the formula V generated in this way then reacts with the allyl alcohol of the formula IV, giving the 5-hydroxymethylisoxazoline of the formula III.

The reaction of the nitrile oxide of the formula V with an allyl alcohol of the formula IV is usually carried out at temperatures of from −30° C. to 80° C., preferably from −10° C. to 20° C., in an inert organic solvent [cf. Houben-Weyl, Methoden der organischen Chemie, Vol. E 5, 1985, 1607 ff. and literature cited therein].

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitrites, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, dimethyl sulfoxide, dimethylformamide and dimethylacetamide.

It is also possible to use mixtures of the solvents mentioned.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use an excess of IV, based on V.

The reaction mixtures are worked up in a customary manner, for example by mixing with water, separating the phases and, if appropriate, chromatographic purification of the crude products. Some of the intermediates and end products are obtained in the form of viscous oils which can be freed from volatile components or purified under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion.

The corresponding aldoximes of the formula VII are known from the literature [cf. Houben-Weyl, Methoden der organischen Chemie, Vol. 10/4, 1968, p. 55 ff.], or they can be prepared from the corresponding aldehydes, in accordance with the literature cited.

The allyl alcohols of the formula IV required for preparing the 5-hydroxymethylisoxazolines III are known from the literature [cf. EP-514 987; Houben-Weyl, Methoden der organischen Chemie, Vol. 6/1a, 1979, p. 55 ff. and literature cited therein] or they can be prepared in accordance with the literature cited.

Process B

A nitrile oxide of the formula V reacts with an allyl derivative of the formula VIII to give a methyl isoxazoline derivative of the formula IX. This is then etherified with an arylmethyl alcohol of the formula X to give the 3-heteroaryl-substituted isoxazoline of the formula I:

L² in the formulae VIII and IX is a nucleophilically displaceable leaving group, such as halogen (e.g. chlorine, bromine or iodine), C₁-C₆-alkylsulfonyloxy or C₁-C₆-haloalkylsulfonyloxy, such as, for example, trifluoromethylsulfonyloxy, or another equivalent leaving group.

The reaction of the methylisozoline derivative of the formula IX with an arylmethyl alcohol of the formula X is carried out analogously to the reaction of the 5-hydroxymethylisoxazoline of the formula III with an arylmethyl derivative of the formula II in process A.

The arylmethyl alcohols of the formula X required for preparing the 3-heteroaryl-substituted isoxazolines of the formula I are known to the person skilled in the art or can be prepared by reactions known from the literature.

The preparation of the methylisoxazoline derivatives of the formula IX from nitrile oxides of the formula V and allyl derivatives of the formula VIII is carried out analogously to the preparation of the 5-hydroxymethylisoxazolines of the formula III in process A.

Furthermore, it is possible to prepare the methylisoxazoline derivatives of the formula IX from 5-hydroxymethylisoxazolines of the formula III:

The conversion of the 5-hydroxymethylisoxazolines into methylisoxazoline derivatives of the formula IX is usually carried out at temperatures of from −20° C. to the reflux temperature of the reaction mixtures in question, in an inert solvent.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran. It is also possible to use mixtures of the solvents mentioned.

Suitable activating agents are, for example, halogenating agents, such as thionyl chloride, phosgene, diphosgene, triphosgene, oxalyl chloride, thionyl bromide, oxalyl bromide, or, for example, alkylsulfonyl chlorides, such as, for example, methylsulfonyl chloride, or haloalkylsulfonyl chlorides, such as, for example, trifluoromethylsulfonyl chloride.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to employ an excess of activating agent.

The allyl derivatives of the formula VIII are known to the person skilled in the art or can be prepared, for example, from the allyl alcohols of the formula IV, analogously to the conversion of III into IX.

Process C

An allyl alcohol of the formula IV is converted with arylmethyl derivative of the formula II into an arylmethyl allyl ether of the formula XI. This then reacts with a nitrile oxide of the formula V to give the 3-heteroaryl-substituted isoxazolines of the formula I:

L¹ in formula II is a nucleophilically displaceable leaving group, such as halogen (e.g. chlorine, bromine or iodine), aryl-, C₁-C₆-alkylsulfonyl, arylsulfonyl, (e.g. toluolsulfonyl), C₁-C₆-haloalkylsulfonyl, C₁C₆-alkylsulfonyloxy or C₁-C₆-haloalkylsulfonyloxy (such as e.g. trifluoromethylsulfonyloxy), or another equivalent leaving group.

The reaction of the arylmethyl allyl ethers of the formula XI with a nitrile oxide of the formula V to give the 3-heteroaryl-substituted isoxazolines of the formula I is carried out analogously to the reaction of the nitrile oxide of the formula V with an allyl alcohol of the formula IV in process A.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to employ an excess of XI, based on V.

Work-up and isolation of the products can be carried out in a manner known per se.

The nitrile oxides of the formula V required for preparing the 3-heteroaryl-substituted isoxazolines of the formula I are obtainable analogously to process A.

The reaction of the allyl alcohol of the formula IV with an arylmethyl derivative of the formula II is carried out analogously to the reaction of the 5-hydroxymethylisoxazoline of the formula III with an arylmethyl derivative of the formula II in process A.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to employ an excess of II, based on IV.

Work-up and isolation of the products can be carried out in a manner known per se.

The arylmethyl derivatives of the formula II and allyl alcohols of the formula IV required for preparing the allylmethyl allyl ethers of the formula XI can be obtained according to process A.

Furthermore, it is possible to prepare the arylmethyl allyl ether of the formula XI by reacting the corresponding allyl derivative of the formula VIII with an arylmethyl alcohol of the formula X (cf. process B).

The reaction is carried out analogously to the reaction of the allyl alcohol of the formula IV with an arylmethyl derivative of the formula II, or analogously to the reaction of 5-hydroxymethylisoxazoline of the formula III with an arylmethyl derivative of the formula II in process A.

The allyl derivatives of the formula VIII and arylmethyl alcohols of the formula X required can be obtained according to process B.

5-Hydroxymethylisoxazolines of the formula III

where X, R¹, R², R³, R⁴ and R⁵ are as defined in claim 1 also form part of the subject-matter of the present invention.

With respect to the variables, the particularly preferred embodiments of the intermediates correspond to those of the radicals X, R¹, R², R³, R⁴ and R⁵ of formula I.

Particular preference is given to 5-hydroxymethylisoxazolines of the formula III, in which

-   X is 6-membered heteroaryl having one to three nitrogen atoms;     -   preferably 6-membered heteroaryl having one or two nitrogen         atoms;     -   in particular pyridyl, pyrimidyl and pyrazinyl;     -   very preferably pyridyl and pyrimidyl;     -   also preferably pyridyl and pyrazinyl;     -   where the 6-membered heteroaryl is substituted in each case as         described above; and -   R¹-R⁵ are hydrogen, C₁-C₄-alkyl, such as, for example, methyl or     ethyl, or C₁-C₄-haloalkyl, such as, for example, difluoromethyl,     trifluoromethyl or trichloromethyl;     -   particularly preferably hydrogen, methyl or trifluoromethyl;     -   very preferably hydrogen;     -   with particular preference, R¹, R², R⁴-R⁵ are hydrogen, methyl         or trifluoromethyl and R³ is hydrogen, methyl, ethyl or         trifluoromethyl;     -   with very particular preference, R¹, R², R⁴-R⁵ are hydrogen and         R³ is methyl.

Particular preference is also given to 5-hydroxymethylisoxazolines of the formula III in which

-   X is X¹, where -   R^(a) is halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino,     C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,     C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl, -   R^(b) is hydrogen or one of the substituents mentioned above under     R^(a); -   R^(d) is hydrogen or C₁-C₆-alkyl;     -   preferably hydrogen or C₁-C₄-alkyl;         with particular preference -   R^(a) is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or     C₁-C₆-haloalkoxy; -   R^(b) is hydrogen, halogen, C₁-C₆-alkyl, C₁-c₆-haloalkyl,     C₁-C₆-alkoxy or C₁-C₆-haloalkoxy; -   R^(d) is hydrogen or C₁-C₄-alkyl; and -   R¹-R⁷ are hydrogen, C₁-C₄-alkyl, such as, for example, methyl or     ethyl, or C₁-C₄-haloalkyl, such as, for example, difluoromethyl,     trifluoromethyl or trichloromethyl;     -   particularly preferably hydrogen, methyl or trifluoromethyl;     -   very preferably hydrogen;     -   with particular preference R¹, R², R⁴-R⁷ are hydrogen, methyl or         trifluoromethyl and R³ is hydrogen, methyl, ethyl or         trifluoromethyl;     -   with very particular preference, R¹, R², R⁴-R⁷ are hydrogen and         R³ is methyl.

Particular preference is also given to the 5-hydroxymethylisoxazolines of the formula III, in which

-   X is X⁵, where -   R^(a) is halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino,     C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,     C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl, -   R^(b), R^(c) are hydrogen or one of the substituents mentioned above     under R^(a); and -   R^(d) is hydrogen or C₁-C₆-alkyl;     -   preferably hydrogen or C₁-C₄-alkyl;         preferably -   R^(a) is halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino,     C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,     C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl; -   R^(b), R^(c) are hydrogen or one of the substituents mentioned above     under R^(a); and -   R^(d) is hydrogen or C₁-C₄-alkyl;     where the 5-membered heterocycle is attached to the isoxazoline     skeleton in the position ortho to the heteroatom;     with particular preference -   R^(a) is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or     C₁-C₆-haloalkoxy; -   R^(b), R^(c) are hydrogen, or one of the substituents mentioned     above under R^(a); and -   R^(d) is hydrogen or C₁-C₄-alkyl;     where the 5-membered heterocycle is attached to the isoxazoline     skeleton in the position ortho to the heteroatom; and -   R¹-R⁵ are hydrogen, C₁-C₄-alkyl, such as, for example, methyl or     ethyl, or C₁-C₄-haloalkyl, such as, for example, difluoromethyl,     trifluoromethyl or trichloromethyl;     -   particularly preferably hydrogen, methyl or trifluoromethyl;     -   very preferably hydrogen;     -   with particular preference, R¹, R², R⁴-R⁵ are hydrogen, methyl         or trifluoromethyl and R³ is hydrogen, methyl, ethyl or         trifluoromethyl;     -   with very particular preference, R¹, R², R⁴-R⁵ are hydrogen and         R³ is methyl.

Particular preference is also given to 5-hydroxymethylisoxazolines of the formula III, in which

-   X is X⁶, where -   R^(a) is halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino,     C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,     C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl; -   R^(b) is hydrogen, or one of the substituents mentioned above under     R^(a);     preferably -   R^(a) is halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino,     C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,     C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl, -   R^(b) is hydrogen, or one of the substituents mentioned above under     R^(a);     where the 5-membered heterocycle is attached to the isoxazoline     skeleton in the position ortho to a heteroatom;     with particular preference -   R^(a) is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or     C₁-C₆-haloalkoxy, -   R^(b) is hydrogen, or one of the substituents mentioned above under     R^(a);     where the 5-membered heterocycle is attached to the isoxazoline     skeleton in the position ortho to a heteroatom; and -   R¹-R⁵ are hydrogen, C₁-C₄-alkyl, such as, for example, methyl or     ethyl, or C₁-C₄-haloalkyl, such as, for example, difluoromethyl,     trifluoromethyl or trichloromethyl;     -   particularly preferably hydrogen, methyl or trifluoromethyl;     -   very preferably hydrogen;     -   with particular preference, R¹, R², R⁴-R⁵ are hydrogen, methyl         or trifluoromethyl and R³ is hydrogen, methyl, ethyl or         trifluoromethyl;     -   with very particular preference, R¹, R², R⁴-R⁵ are hydrogen and         R³ is methyl.

The present invention also provides methylisoxazolines of the formula IX

where X and R¹-R⁵ are as defined in claim 1 and L² is a nucleophilically displaceable leaving group, such as halogen (for example chlorine, bromine and iodine), C₁-C₆-alkylsulfonyloxy or C₁-C₆-haloalkylsulfonyloxy (for example trifluoromethylsulfonyloxy), or another equivalent leaving group.

With respect to the variables, the particularly preferred embodiments of the intermediates correspond to those of radicals X and R¹-R⁵ of the formula I.

Particular preference is given to methylisoxazolines of the formula IX in which

-   X is 6-membered heteroaryl having one to three nitrogen atoms;     -   in particular 6-membered heteroaryl having one or two nitrogen         atoms;     -   very preferably pyridyl;     -   where the 6-membered heteroaryl is substituted as described         above; and -   R¹-R⁵ are hydrogen, C₁-C₄-alkyl, such as, for example, methyl or     ethyl, or C₁-C₄-haloalkyl, such as, for example, difluoromethyl,     trifluoromethyl or trichloromethyl;     -   particularly preferably hydrogen, methyl or trifluoromethyl;     -   very preferably hydrogen;     -   with particular preference, R¹, R², R⁴-R⁵ are hydrogen, methyl         or trifluoromethyl and R³ is hydrogen, methyl, ethyl or         trifluoromethyl;     -   with very particular preference, R¹, R², R⁴-R⁵ are hydrogen and         R³ is methyl; and -   L² is a nucleophilically displaceable leaving group; preferably     halogen, C₁-C₆-alkylsulfonyloxy or C₁-C₆-haloalkylsulfonyloxy;     -   particularly preferably chlorine, bromine, iodine or         trifluoromethylsulfonyloxy.

3-(2-Chloropyrid-3-yl)-4,5-dihydro-5-hydroxy-ethyl-5-methylisoxazole

5.0 g (0.03 mol) of 2-chloropyrid-3-ylcarboxaldehyde oxime were initially charged in dimethylformamide, a spatula tip of N-chlorosuccinimide was added and the mixture was heated at 40-45° C. 4.26 g (0.03 mol) of N-chlorosuccinimide were then added a little at a time such that the reaction temperature did not exceed 50° C. After 1 h of stirring at 45-50° C., the mixture was hydrolyzed and extracted with diethyl ether, and the organic phase was dried. 2.07 g (0.03 mol) of 2-methyl-2-propenol were added to the resulting solution, and 5.37 g (0.04 mol) of triethylamine were added dropwise with ice-cooling. After 1 h, the reaction solution was allowed to warm to room temperature, the precipitate was filtered off and the solvent was removed. This gave 2.8 g (38.7% of theory) of the title compound (m.p. 71° C.).

5-(2,6-Difluorobenzyloxymethyl)-5-methyl-3-(3-propylisoxazol-5-yl)-4,5-dihydroisoxazole

3 g (0.02 mol) of 3-propylisoxazol-5-ylcarbaldehyde oxime were dissolved in 20 ml of dimethylformamide, 0.29 g (0.002 mol) of N-chlorosuccinimide was added and the reaction mixture was heated to 45-50° C. Over a period of one hour, a further 2.31 g (0.02 mol) of N-chlorosuccinimide were added. The reaction mixture was then allowed to cool and subsequently poured into water. The phases were separated and the aqueous phase was extracted with diethyl ether. The combined organic phases were washed and dried, and 3.48 g (0.02 mol) of (2-methyl-prop-2-en)oxymethyl-2,6-difluorobenzene were added. At 0° C., 3 g (0.03 mol) of triethylamine were then slowly added dropwise, and the mixture was stirred at 0° C. for one hour. The resulting precipitate was filtered off and the solvent was removed from the filtrate. Customary purification methods gave 0.8 g (11.7% of theory) of the title compound.

In addition to the compounds above, Tables 2 to 5 list further 5-hydroxymethylisoxazolines of the formula III and 3-heteroaryl-substituted isoxazolines of the formula I which were prepared or are preparable in a manner analogous to the processes described above.

TABLE 2 2

(=III where R¹, R², R⁴, R⁵ = hydrogen R³ = methyl selected ¹H-NMR data No. X [DMSO] or m.p. 2.1 2-chloropyrid-3-yl 71° C. 2.2 6-methylpyrid-2-yl 2.3 2-chloro-5-methylimidazol-4-yl 2.4 3-methylisoxazol-5-yl 2.5 3-propylisoxazol-5-yl 2.6 4-(but-2-yl)isoxazol-5-yl 2.7 3-(2-methylpropyl)isoxazol-5-yl 2.8 3-phenylisoxazol-5-yl 2.9 2-methylthiazol-4-yl 2.10 2-methyl-5-chlorothiazol-4-yl 3.22 (dd, 2H), 3.40 (dd, 2H)

TABLE 3 3

(=I where R¹, R², R⁴-R⁷ = hydrogen R³ = methyl, Y = 2-fluorophenyl) selected ¹H-NMR data [cm⁻¹]DMSO] or m.p. or MS [^(m)/e] or selected IR data No. X [cm⁻¹] 3.1 2-chloropyrid-3-yl 3.31 (dd, 2H), 3.59 (dd, 2H) 3.2 6-methylpyrid-2-yl 3.27 (dd, 2H), 3.53 (dd, 2H) 3.3 2-chloro-5-methylimidazol-4-yl 3.30 (dd, 2H), 3.58 (dd, 2H) 3.4 3-methylisoxazol-5-yl 3.23 (dd, 2H), 3.57 (dd, 2H) 3.5 3-propylisoxazol-5-yl 3.25 (dd, 2H), 3.55 (dd, 2H) 3.6 4-(but-2-yl)isoxazol-5-yl 3.25 (dd, 2H), 3.56 (dd, 2H) 3.7 3-(2-methylpropyl)isoxazol-5-yl [M + H] + 346 3.8 3-phenylisoxazol-5-yl 90° C. 3.9 2-methylthiazol-4-yl 3.32 (dd, 2H), 3.52 (dd, 2H) 3.10 2-methyl-5-chlorothiazol-4-yl 3.22 (dd, 2H), 3.50 (dd, 2H) 3.11 4-chloropyrid-3-yl 3.35 (dd, 2H), 3.59 (dd, 2H) 3.12 2-chlorid-3-yl N-oxide IR [cm⁻¹] 1259 N-oxide 3.13 2,4-dichloropyrid-3-yl 3.15 (dd, 2H), 3.60 (dd, 2H) 3.14 2,6-dichloropyrid-3-yl 3.32 (dd, 2H), 3.56 (dd, 2H) 3.15 2-bromopyrid-3-yl 3.28 (dd, 2H), 3.58 (dd, 2H) 3.16 2-methylpyrid-3-yl 3.28 (dd, 2H), 3.56 (dd, 2H) 3.17 2-trifluoromethylpyrid-3-yl 3.26 (dd, 2H), 3.58 (dd, 2H) 3.18 4-trifluoromethyipyrid-3-yl 3.3 (dd, 2H), 3.55 (dd, 2H) 3.19 2-methoxypyridin-3-yl 3.27 (dd, 2H), 3.54 (dd, 2H) 3.20 6-methoxypyridin-3-yl 3.25 (dd, 2H), 3.53 (dd, 2H) 3.21 2-chloro-4-isopropylpyrid-3-yl 3.3 (dd, 2H), 3.55 (dd, 2H) 3.22 2-chloro-6-methylpyrid-3-yl 3.35 (dd, 2H), 3.54 (dd, 2H) 3.23 2-chloro-4,6-dimethyl-pyrid-3-yl 3.12 (dd, 2H), 3.57 (dd, 2H) 3.24 2,6-dichloro-4-methyl-pyridin-3-yl 3.18 (dd, 2H), 3.59 (dd, 2H) 3.25 3-chloropyrid-4-yl 3.32 (dd, 2H), 3.62 (dd, 2H) 3.26 3-bromopyrid-4-yl 3.38 (dd, 2H), 3.58 (dd, 2H) 3.27 2-methylpyrid-4-yl 3.24 (dd, 2H), 3.58 (dd, 2H) 3.28 3-trifluoromethylpyrid-4-yl 3.25 (dd, 2H), 3.57 (dd, 2H) 3.29 2-trifluoromethyl-5-chloro- 3.43 (dd, 2H), 3.59 (dd, 2H) pyrid-4-yl 3.30 2-cyclopropylpyrimidin-4-yl 3.25 (dd, 2H), 3.58 (dd, 2H) 3.31 2-phenyl-4-methyl-pyrimidin-6-yl 3.35 (dd, 2H), 3.60 (dd, 2H) 3.32 3-chloropyrazin-2-yl 3.4 (dd, 2H), 3.68 (dd, 2H) 3.33 1-methyl-4,5-dichloroimidazol-2-yl 3.24 (dd, 2H), 3.57 (dd, 2H) 3.34 1,4-dimethyl-2-chloroimidazol-2-yl 3.31 (dd, 2H), 3.57 (dd, 2H) 3.35 3-methyl-4-chloroisoxazol-5-yl 3.28 (dd, 2H), 3.57 (dd, 2H) 3.36 ″2-chloropyrid-3-yl″ 1492, 1456, 1351, 1194, methylsulfonic acid salt 1058, 785, 772, 761, 536

TABLE 4 4

(=I where R¹, R², R⁴-R⁷ = hydrogen R³ = methyl, Y = 2,6-difluorophenyl selected ¹H-NMR data No. X [DMSO] or m.p. or MS [^(m)/e] 4.1 2-chloropyrid-3-yl 3.33 (dd, 2H), 3.53 (dd, 2H) 4.2 6-methylpyrid-2-yl 70° C. 4.3 2-chloro-5-methylimidazol-4-yl [M + H] + 356 4.4 3-methylisoxazol-5-yl 3.20 (dd, 2H), 3.54 (dd, 2H) 4.5 3-propylisoxazol-5-yl 3.22 (dd, 2H), 3.52 (dd, 2H) 4.6 4-(but-2-yl)isoxazol-5-yl 3.18 (dd, 2H), 3.53 (dd, 2H) 4.7 3-(2-methylpropyl)isoxazol-5-yl 3.19 (dd, 2H), 3.53 (dd, 2H) 4.8 3-phenylisoxazol-5-yl 79-81° C. 4.9 2-methylthiazol-4-yl 3.18 (dd, 2H), 3.51 (dd, 2H) 4.10 2-methyl-5-chlorothiazol-4-yl 3.22 (dd, 2H), 3.50 (dd, 2H) 4.11 3-chloropyrid-2-yl m.p. 102° C. 4.12 3-methylpyrid-2-yl 3.34 (dd, 2H), 3.55 (dd, 2H) 4.13 trifluoromethylpyrid-2-yl m.p. 95-96° C. 4.14 2-fluoropyrid-3-yl 3.26 (dd, 2H), 3.53 (dd, 2H) 4.15 2-fluoropyrid-3-yl 3.32 (dd, 2H), 3.56 (dd, 2H) 4.16 2-bromopyrid-3-yl 3.22 (dd, 2H), 3.55 (dd, 2H) 4.17 2,4-dichloropyrid-3-yl 3.09 (dd, 2H), 3.59 (dd, 2H) 4.18 2,4-dichloropyrid-3-yl 3.28 (dd, 2H), 3.56 (dd, 2H) 4.19 2-chloropyrid-3-yl N-oxide [M]⁺ 368 4.20 2-cyanopyrid-3-yl 3.48 (dd, 2H), 3.61 (dd, 2H) 4.21 2-hydroxypyrid-3-yl 3.38 (dd, 2H), 3.52 (dd, 2H) 4.22 2-nitropyrid-3-yl 3.08 (dd, 2H), 3.60 (dd, 2H) 4.23 2-methylpyrid-3-yl m.p. 85° C. 4.24 4-methylpyrid-3-yl 3.30 (dd, 2H), 3.57 (dd, 2H) 4.25 2-ethylpyrid-3-yl 3.20 (dd, 2H), 3.58 (dd, 2H) 4.26 2-trifluoromethylpyrid-3-yl 3.20 (dd, 2H), 3.51 (dd, 2H) 4.27 4-trifluoromethylpyrid-3-yl 3.23 (dd, 2H), 3.53 (dd, 2H) 4.28 2-methoxypyrid-3-yl 3.24 (dd, 2H), 3.52 (dd, 2H) 4.29 2(methylthio)pyrid-3-yl m.p. 97-98° C. 4.30 2(methylsulfonyl)pyrid-3-yl IR: 1312 cm⁻¹ (SO₂) 4.31 2(methylsulfonix)pyrid-3-yl ¹³C-NMR: 87.27, 87.20 4.32 2(dimethylamino)pyrid-3-y2. [M + H]⁺ 362 4.33 2(phenylthio)pyrid-3-yl 3.31 (dd, 2H), 3.58 (dd, 2H) 4.34 2-chloro-6-methylpyrid-3-yl 3.3 (dd, 2H), 3.55 (dd, 2H) 4.35 2-chloro-4-isopropylpyrid-3-yl 3.26 (dd, 2H), 3.54 (dd, 2H) 4.36 2-chloro-4,6-dimethyl-pyrid-3-yl 3.11 (dd, 2H), 3.58 (dd, 2H) 4.37 2-methyl-4-chloropyride 3.1 (dd, 2H), 3.54 (dd, 2H) 4.38 3-chloropyrid-4-yl 3.34 (dd, 2H), 3.56 (dd, 2H) 4.39 3-bromopyrid-4-yl 3.3 (dd, 2H), 3.55 (dd, 2H) 4.40 3-trifluoromethylpyrid-4-yl 3.25 (dd, 2H), 3.55 (dd, 2H) 4.41 2-trifluoromethyl-5-chloro- m.p. 60° C. pyrid-4-yl 4.42 2-methylpyrimidin-4-yl m.p. 89° C. 4.43 2-cyclopropylpyrimidin-4-yl 3.26 (dd, 2H), 3.58 (dd, 2H) 4.44 3-chloropyrazin-2-yl 3.3 (dd, 2H), 3.58 (dd, 2H) 4.45 5-methylfuran-2-yl 3.03 (dd, 2H), 3.46 (dd, 2H) 4.46 3-chloro-5-chloromethylfuran-2-yl 3.24 (dd, 2H), 3.58 (dd, 2H) 4.47 3-methoxycarbonylfuran-2-yl 3.3 (dd, 2H), 3.54 (dd, 2H) 4.48 1-methyl-4,5-dichloroimidazol-2-yl m.p. 86° C. 4.49 3-methyl-4-chloroisoxazol-5-yl 3.3 (dd, 2H), 3.54 (dd, 2H) 4.50 1-methyl-3,5-dichloropyrrol-2-yl [M + H]⁺ 389 4.51 2-ethenylpyrid-3-yl 3.3 (dd, 2H), 3.54 (dd, 2H) 4.52 2-acetylpyrid-3-yl [M + H]⁺ 361

TABLE 5 5

(I where R¹, R², R⁴-R⁷ = hydrogen, R³ = methyl) selected ¹H-NMR No. X Y data or MS 5.1 2-chloropyrid-3-yl phenyl 3.4 (dd, 2H), 3.56 (dd, 2H) 5.2 2-chloropyrid-3-yl 3-fluorophenyl 335 [M + H]⁺ 5.3 2-chloropyrid-3-yl 2-chlorophenyl 351 [M + H]⁺ 5.4 2-chloropyrid-3-yl 2,6-dichlorophenyl 385 [M + H]⁺ 5.5 2-chloropyrid-3-yl 2,3,6-trichlorophenyl 419 [M + H]⁺ 5.6 2-chloropyrid-3-yl 2-chloro-6-fluoro- 3.28 (dd, 2H), 3.56 phenyl (dd, 2H) 5.7 2-chloropyrid-3-yl 4-methylphenyl 331 [M + H]⁺ 5.8 2-chloropyrid-3-yl 2-methylnaphthyl-1-yl 381 [M + H]⁺ 5.9 2-chloropyrid-3-yl 5-chloro-1-methyl-3- 423 [M + H]⁺ trifluoromethyl- pyrazol-4-yl Use

The 3-heteroaryl-substituted isoxazolines of the formula I and their agriculturally useful salts are suitable, both in the form of isomer mixtures and in the form of the pure isomers, as herbicides. The herbicidal compositions comprising compounds of the formula I control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and harmful grasses in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.

Depending on the application method used, the compounds of the formula I or the herbicidal compositions comprising them can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds of the formula I may also be used in crops which tolerate the action of herbicides owing to breeding, including genetic engineering methods.

The compounds of the formula I, or the herbicidal compositions comprising them, can be used for example in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly-concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting or granules, by means of spraying, atomizing, dusting, broadcasting or watering. The use forms depend on the intended aims; in any case, they should ensure a very fine distribution of the active compounds according to the invention.

The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I and auxiliaries customary for formulating crop protection agents.

Essentially, suitable inert auxiliaries include: mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. amines such as N-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the substrates, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is also possible to prepare concentrates consisting of active substance, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.

Suitable surfactants (adjuvants) are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, e.g. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene, or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl polyglycol ether or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors or methylcellulose.

Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the compounds of the formula I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise from about 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound. The active compounds are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to the NMR spectrum).

The production of such preparations is illustrated by the following formulation examples:

-   I. 20 parts by weight of an active compound of the formula I are     dissolved in a mixture consisting of 80 parts by weight of alkylated     benzene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene     oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight     of calcium dodecylbenzenesulfonate and 5 parts by weight of the     adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring     the solution into 100,000 parts by weight of water and finely     distributing it therein gives an aqueous dispersion which comprises     0.02% by weight of the active compound of formula I. -   II. 20 parts by weight of an active compound of the formula I are     dissolved in a mixture consisting of 40 parts by weight of     cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight     of the adduct of 7 mol of ethylene oxide to 1 mol of isooctylphenol     and 10 parts by weight of the adduct of 40 mol of ethylene oxide to     1 mol of castor oil. Pouring the solution into 100,000 parts by     weight of water and finely distributing it therein gives an aqueous     dispersion which comprises 0.02% by weight of the active compound of     formula I. -   III. 20 parts by weight of an active compound of the formula I are     dissolved in a mixture consisting of 25 parts by weight of     cyclohexanone, 65 parts by weight of a mineral oil fraction of     boiling point 210 to 280° C. and 10 parts by weight of the adduct of     40 mol of ethylene oxide to 1 mol of castor oil. Pouring the     solution into 100,000 parts by weight of water and finely     distributing it therein gives an aqueous dispersion which comprises     0.02% by weight of the active compound of formula I. -   IV. 20 parts by weight of an active compound of the formula I are     mixed thoroughly with 3 parts by weight of sodium     diisobutylnaphthalenesulfonate, 17 parts by weight of the sodium     salt of lignosulfonic acid from a sulfite waste liquor and 60 parts     by weight of pulverulent silica gel, and the mixture is ground in a     hammer mill. Finely distributing the mixture in 20,000 parts by     weight of water gives a spray mixture which comprises 0.1% by weight     of the active compound of formula I. -   V. 3 parts by weight of an active compound of the formula I are     mixed with 97 parts by weight of finely divided kaolin. This gives a     dust which comprises 3% by weight of the active compound of formula     I. -   VI. 20 parts by weight of an active compound of the formula I are     mixed intimately with 2 parts by weight of calcium     dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol     polyglycol ether, 2 parts by weight of the sodium salt of a     phenol/urea/formaldehyde condensate and 68 parts by weight of a     paraffinic mineral oil. This gives a stable oily dispersion. -   VII. 1 part by weight of an active compound of the formula I is     dissolved in a mixture consisting of 70 parts by weight of     cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and     10 parts by weight of ethoxylated castor oil. This gives a stable     emulsion concentrate. -   VIII. 1 part by weight of an active compound of the formula I is     dissolved in a mixture of 80 parts by weight of cyclohexanone and 20     parts by weight of Wettol® EM 31 (=nonionic emulsifier based on     ethoxylated castor oil). This gives a stable emulsion concentrate.

The compounds of the formula I or the herbicidal compositions can be applied pre- or post-emergence. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that they come into contact as little as possible, if at all, with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).

The application rates of the compound of the formula I are from 0.001 to 3.0, preferably from 0.01 to 1.0 kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage.

To widen the activity spectrum and to achieve synergistic effects, the 3-heteroaryl-substituted isoxazolines of the formula I may be mixed with a large number of representatives of other herbicidal or growth-regulating active compound groups and are applied concomitantly. Suitable components for mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, (hetero)aryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-(hetaroyl/aroyl)-1,3-cyclohexanediones, heteroarylaryl ketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ether, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.

It may furthermore be advantageous to apply the compounds of the formula I, alone or else concomitantly in combination with other herbicides, or in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added.

USE EXAMPLES

The herbicidal activity of 3-heteroaryl-substituted isoxazolines of the formula I was demonstrated by the following greenhouse experiments:

The cultivation containers used were plastic flower pots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, directly after sowing the active compounds, which had been suspended or emulsified in water, were applied by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this was adversely affected by the active compounds. The application rate for the post-emergence treatment was 3.0 kg/ha a.s. (active substance).

For the post-emergence treatment, the test plants were first grown to a height of from 3 to 15 cm, depending on the plant habit, and only then treated with the active compounds which had been suspended or emulsified in water. The test plants were for this purpose either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the above-ground parts and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments were of the following species:

Scientific name Common name Abutilon theophrasti velvet leaf Avena fatua wild oat Lolium multiflorum Italian ryegrass Setaria italica foxtail millet

At application rates of 3.0 kg/ha, the compounds 3.16, 3.17, 3.27, 3.36, 4.29 and 4.38 showed very good preemergence activity in the harmful plants Solium multiflorum and Setaria italica.

At application rates of 3.0 kg/ha, the pre-emergence activity of compound 4.1 on the harmful plants Lolium multiflorum and Setaria italica is very good.

At application rates of 3.0 kg/ha, the compound 4.1 showed very good post-emergence activity in the unwanted plants Abutilon theophrasti, Avena fatua and Setaria italica. 

1. A 3-heteroaryl-substituted isoxazoline of the formula I

where: X is pyridyl, which is partially or fully halogenated and/or carries one to three substituents selected from the following group: cyano, nitro, hydroxyl, C₁-C₈-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₁-C₈-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₈-cyanoalkyl, C₂-C₈-cyanoalkenyl, C₁-C₈-alkoxy, C₁-C₈-haloalkoxy, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkoxy-C₁-C₈-alkoxy, amino, C₁-C₈-alkylamino, di(C₁-C₈-alkyl)amino, C₁-C₈-alkylcarbonylamino, N—C₁-C₈-alkylcarbonyl-N—C₁-C₈-alkylamino, C₁-C₈-alkoxycarbonylamino, N—C₁-C₈-alkoxycarbonyl-N—C₁-C₈-alkylamino, amino-C₁-C₈-alkyl, C₁-C₈-alkylamino-C₁-C₈-alkyl, di(C₁-C₈-alkyl)amino-C₁-C₈-alkyl, C₁-C₈-alkylthio, C₁-C₈-haloalkylthio, C₁-C₈-alkylthio-C₁-C₈-alkyl, C₁-C₈-alkylsulfinyl, C₁-C₈-haloalkylsulfinyl, C₁-C₈-alkylsulfonyl, C₁-C₈-haloalkylsulfonyl, C₁-C₈-alkylsulfonyl-C₁-C₈-alkyl, C₁-C₈-alkylcarbonyl, C₁-C₈-alkoxycarbonyl, C₁-C₈-alkoxycarbonyl-C₁-C₈-alkyl, aminocarbonyl, C₁-C₈-alkylaminocarbonyl, di(C₁-C₈-alkyl)aminocarbonyl, aminocarbonyl-C₁-C₈-alkyl, C₁-C₈-alkylaminocarbonyl-C₁-C₈-alkyl, di(C₁-C₈-alkyl)aminocarbonyl-C₁-C₈-alkyl, carboxyl, carboxyl-C₁-C₈-alkyl, phenyl, phenoxy, phenylthio, phenylamino, phenyl-C₁-C₈-alkyl and phenyl-C₁-C₈-alkoxy, where the six last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one to three substituents selected from the group consisting of nitro, cyano, C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-haloalkyl, C₁-C₈-haloalkoxy, C₁-C₈-alkylthio, C₁-C₈-haloalkylthio, C₁-C₈-alkylsulfinyl, C₁-C₈-haloalkylsulfinyl, C₁-C₈-alkylsulfonyl and C₁-C₈-haloalkylsulfonyl; R¹-R⁷ are hydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl; Y is aryl which may be partially or fully halogenated and/or may carry one to three substituents selected from the group consisting of cyano, nitro, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkoxycarbonyl-C₁-C₄-alkoxy, C₁-C₆-alkylsulfonyl, phenyl, phenoxy and phenylcarbonyl; or an agriculturally useful salt thereof.
 2. A process for preparing 3-heteroaryl-substituted isoxazolines of the formula I as claimed in claim 1, which comprises reacting an arylmethyl allyl ether of the formula XI

where X and R¹-R⁷ are as defined in claim 1, with an nitride oxide formula V X—≡N—O  V, where X is as defined in claim
 1. 3. A composition, comprising a herbicidally effective amount of at least one or more 3-heteroaryl-substituted isoxazoline(s) of the formula I or an agriculturally useful salt of I as claimed in claim 1 and auxiliaries customary for formulating crop protection agents.
 4. A method for controlling unwanted vegetation, which comprises allowing a herbicidally effective amount of one or more 3-heteroaryl-substituted isoxazoline(s) of the formula I as claimed in claim 1 or an agriculturally useful salt of I to act on plants, their habitat and/or on seeds.
 5. A 3heteroaryl-substituted isoxazoline of the formula I as claimed in claim 1, wherein X is pyridyl, which is attached to the isoxazoline skeleton in a position ortho or meta to a ring nitrogen, and which is partially or fully halogenated and/or carries one or two substituents selected from the following group: cyano, nitro hydroxyl, C₁-C₈-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocy-cloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₁-C₈-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆haloalkynyl, C₁-C₈-cyanoalkyl, C₂-C₈-cyanoalkenyl, C₁-C₈-alkoxy, C₁-C₈-haloalkoxy, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkoxy-C₁-C₈-alkoxy, amino, C₁-C₈-alkylamino, di(C₁-C₈-alkyl)amino, C₁-C₈-alkylcarbonylamino, N—C₁-C₈-alkylcarbonyl-N—C₁-C₈-alkylamino, C₁-C₈-alkoxycarbonylamino, N—C₁-C₈-alkoxycarbonyl-N—C₁-C₈alkylamino, amino-C₁-C₈-alkyl, C₁-C₈-alkylamino-C₁-C₈-alkyl, di(C₁-C₈-alkyl)amino-C₁-C₈-alkyl, C₁-C₈-alkylthio, C₁-C₈-haloalkylthio, C₁-C₈-alkylthio-C₁-C₈-alkyl, C₁-C₈-alkylsulfinyl, C₁-C₈-haloalkylsulfinyl, C₁-C₈-alkylsulfonyl, C₁-C₈-haloalkylsulfonyl, C₁-C₈-alkylsulfonyl-C₁-C₈-alkyl, C₁-C₈-alkylcarbonyl, C₁-C₈-alkoxycarbonyl, C₁-C₈-alkoxycarbonyl-C₁-C₈-alkyl, aminocarbonyl, C₁-C₈-alkylaminocarbonyl, di(C₁-C₈-alkyl)aminocarbonyl, aminocarbonyl-C₁-C₈-alkyl, C₁-C₈-alkylaminocarbonyl-C₁-C₈-alkyl, di(C₁-C₈-alkyl)aminocarbonyl-C₁-C₈-alkyl, carboxyl and carboxyl-C₁-C₈-alkyl.
 6. A 3-heteroaryl-substituted isoxazoline of the formula I as claimed in claim 1, wherein X is pyridyl, which is attached to the isoxazoline skeleton in a position ortho or meta to a ring nitrogen, and which is partially or fully halogenated and/or carries in a position ortho to a nitrogen atom, one or two substituents selected from the following group: cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio and C₁-C₆-alkyl-sulfinyl.
 7. A 3-heteroaryl-substituted isoxazoline of the formula I as claimed in claim 1, wherein X is pyridyl, which is partially or fully halogenated and/or carries one to three substituents selected from the following group: cyano, nitro hydroxyl, C₁-C₈-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₁-C₈-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₈-cyanoalkyl, C₂-C₈-cyanoalkenyl, C₁-C₈-alkoxy, C₁-C₈-haloalkoxy, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkoxy-C₁-C₈-alkoxy, amino, C₁-C₈-alkylamino, di(C₁-C₈-alkyl)amino, C₁-C₈-alkylcarbonylamino, N—C₁-C₈-alkylcarbonyl-N—C₁-C₈-alkylamino, C₁-C₈-alkoxycarbonylamino, N—C₁-C₈-alkoxycarbonyl-N—C₁-C₈-alkylamino, amino-C₁-C₈-alkyl, C₁-C₈-alkylamino-C₁-C₈-alkyl, di(C₁-C₈-alkyl)amino-C₁-C₈-alkyl, C₁-C₈-alkylthio, C₁-C₈-haloalkylthio, C₁-C₈-alkylthio-C₁-C₈-alkyl, C₁-C₈-alkylsulfinyl, C₁-C₈-haloalkylsulfinyl, C₁-C₈-alkylsulfonyl, C₁-C₈-haloalkylsulfonyl, C₁-C₈-alkylsulfonyl-C₁C₈-alkyl, C₁-C₈-alkylcarbonyl, C₁-C₈-alkoxycarbonyl, C₁-C₈-alkoxycarbonyl-C₁-C₈-alkyl, aminocarbonyl, C₁-C₈-alkylaminocarbonyl, di(C₁-C₈-alkyl)aminocarbonyl, aminocarbonyl-C₁-C₈-alkyl, C₁-C₈-alkylaminocarbonyl-C₁-C₈-alkyl, di(C₁-C₈-alkyl)aminocarbonyl-C₁-C₈-alkyl, carboxyl and carboxyl-C₁-C₈-alkyl.
 8. A 3-heteroaryl-substituted isoxazoline of the formula I as claimed in claim 1, wherein Y is phenyl, which may be partially or fully halogenated and/or may carry one to three substituents selected from the group consisting of: cyano, nitro, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkoxycarbonly-C₁-C₄-alkoxy, C₁-C₆-alkylsulfonyl, phenyl, phenoxy and phenylcarbonyl.
 9. A 3-heteroaryl-substituted isoxazoline of the formula I as claimed in claim 1, wherein Y is phenyl, which is halogenated in the 2- and/or 6-position to a point of attachment and/or may carry one substituent from the group consisting of cyano, C₁-C₄-alkyl and C₁-C₄-halogenalkyl.
 10. A 3heteroaryl-substituted isoxazoline of the formula I as claimed in claim 1, wherein the pyridyl ring X is attached to the isoxazoline skeleton in a position ortho or meta to the ring nitrogen of the pyridyl.
 11. A 3heteroaryl-substituted isoxazoline of the formula I as claimed in claim 1, wherein the pyridyl ring X is attached to the isoxazoline skeleton in a position meta to the ring nitrogen of the pyridyl. 